While I personally still ponder and consider that a simple interface to allow dissemination of licensing information including a pick-a-license chooser can be designed, the approach of tldrlegal and the website have many many issues.

To exemplify, the over simplistic categorization is often essentially inaccurate. Criteria such as "sublicense" or "place warranty" are misleading and of no real interest for individual developers. (no one prevents others to place warranty; sublicensing is usually either ignored or a source of confusion in open licensing)
If, as the project draft states, the purpose is to reduce disrespect for licenses, reducing inaccurate information should be a good place to start.

To participate in the project, the site imposes on contributors a huge, hard to read, cumbersome legal document: its terms of service. A couple of examples from it:
"You may use the Sites only for your personal use." I don't know what that means. Am I supposed to choose only licenses for personal use, not contribute on behalf on an employer, something else?
"You hereby designate TLDR and its contributors as the sole “Attribution Party” under Section 4(b) of the CC-BY license to attribute your Contribution as part of the collective Content of the Sites. With this designation, you release TLDR from the obligation to specifically attribute your Contributions to you." - ... I don't think it's a good idea to try to avoid attributing the contributing authors for their work. On another note, it doesn't specify which CC-BY. For a site dedicated to licensing, it's unexpected.
"You may not make, sell, offer for sale, modify, reproduce, display, publicly perform, import, distribute, retransmit or otherwise use the Content in any way, unless expressly permitted to do so by TLDR." - so tldrlegal wants contributions under a "CC-BY" which is stripping authors from the "BY", then turn around and use their work in order to disallow them and everyone else from the core rights of a sharing license.

I suggest tldrlegal to reconsider their terms of service, to make them more inline with the declared mission of this project and friendlier to potential participation, and if this is going to become an OSI project (or has it already?), then with OSI mission.

Thanks for the answers.

Patrick, that's great, I appreciate the clarification.

Kevin,
If I understand correctly, some of this confusion isn't your intention and can be fixed. The ToU is so full of heavy obligations that it's difficult (for me) to take one by one, I'll try though.

One quick point I'd make, from the ToU and your answer.

 "You may use the Sites only for your personal use." I don't know what that means. Am I supposed to choose only licenses for personal use, not contribute on behalf on an employer, something else?
 After this, the license goes on to state that you may use it for internal business purposes, and for other cases you must ask for permission.  Basically this is to prevent someone from reselling or doing something shady with the site/info.

That's the problem. Is this saying that reselling is something shady, for the content of the site? Lets leave the software infrastructure aside here, but the "info" I guess is the Content. I say this also because the ToU continues by including the Content into the proprietary licensing terms they claim to extend on users:

 none of the Content and/or Information may be reverse-engineered, modified, reproduced, republished, translated into any language or computer language, re-transmitted in any form or by any means, resold or redistributed without the prior written consent of TLDR.

Also:

 You may not make, sell, offer for sale, modify, reproduce, display, publicly perform, import, distribute, retransmit or otherwise use the Content in any way, unless expressly permitted to do so by TLDR.

I thought the ToU (and your reply) says later that this content is supposed to be licensed CC-BY 3.0 by TLDR. Therefore selling it is a permission guaranteed by CC-BY license.

This is not the first site that embeds copyright licensing terms in its Terms of Use, and I find a lot of confusion arising from such practice. In this case, it's utterly unnecessary and contradictory, because apparently the content is licensed CC-BY 3.0. That gives users all permissions to use it (for any purpose, not "personal"), to resell it, to modify it and redistribute it with or without money exchanges. Stating that you have to ask for permission to resell it is incorrect, and concerning.

Concerning, because the site purports to explain CC-BY, here:
https://tldrlegal.com/license/creative-commons-attribution-(cc)
I note that it says "commercial use: Yes". Sorry, I'm not sure how are users supposed to learn what the site says on CC-BY when the site itself denies it in their ToU.

To keep other issues out for the moment, I'd suggest that the solution for this and many similar contradictions is to remove any licensing terms from the ToU, if they refer to the Content. It would clean a lot of it, and we can focus on remaining issues. Unless you feel there's a good reason to keep them, which I think it's equivalent to stating there's something (related to copyright) in the ToU you want which is not covered by CC-BY for Content. If that is the case, I think it would help to determine what exactly is that something?

 “"You hereby designate TLDR and its contributors as the sole “Attribution Party” under Section 4(b) of the CC-BY license to attribute your Contribution as part of the collective Content of the Sites. With this designation, you release TLDR from the obligation to specifically attribute your Contributions to you." - ... I don't think it's a good idea to try to avoid attributing the contributing authors for their work.”
 This, I think, is more for simplicity’s sake.  In referencing TLDRLegal, having one source to point to is much more practical.  Imagine a blog post about the MIT License; it would be more feasible to say “According to TLDRLegal, the MIT License waives liability” instead of “According to TLDRLegal and Bob Smith and Contributor #6 and etc..., the MIT License waives liability”.  We could, however, add that if you include -enough- information, say a full copy of the summary, you must credit authors in the same way we do.
 How TLDRLegal handles credit it is similar to Wikipedia or Github, where we provide a full list of edits, their authors, who accepted the changes and even diffs that were made on every license page (i.e. https://tldrlegal.com/license/mit-license#changesets/accepted).

But this is true anyway: you can always write a blog that references TLDRLegal, and points to the site. That's covered by fair use, not copyright. It's OUTSIDE copyright. "Referencing" is not a copyright permission. One can always reference some text by indicating its known source, it never needs copyright permission for that, so it doesn't need to comply with a copyright license. Copyright applies when a COPY is made (or substantial part), not referencing, informing about it, criticizing it, or whatever.

This is important, I think. You do have your final purpose achieved anyway, and while I agree with you and the simplicity of referencing, I'm saying that you don't have to do anything at all to achieve it.

I can refer to what Firefox does or what its UI says without needing to comply with its copyright license. I don't have to list in my blog its contributors. And Firefox is a random example which has multiple copyright holders and no copyright permission to Mozilla Foundation to strip down attribution from their license.

I can refer to how it's something implemented in Linux kernel without needing to comply with its copyright license. I don't have to list in my blog its contributors. Linux kernel is another random example with multiple substantial copyright holders and no permission to any entity to strip down attribution from their license.

I can refer to what OSI FAQ says without needing to list its contributors, nor its copyright notice. It's a fair use, a use outside copyright. Just another example.

 We could, however, add that if you include -enough- information, say a full copy of the summary, you must credit authors in the same way we do.

Exactly my point: SUBSTANTIAL COPY is covered by copyright. Merely referencing is not, but a copy of enough material is. Then, the copyright license granted by contributors applies. Complying with it would be to credit authors, or possibly, again, to link to TLDR credits.

I see nothing here that justifies a copyright permission to TLDRLegal entity that amounts to lack of credit, and I think suggesting it would be is more like a roundabout incorrect justification to claim that "referencing" (without substantial copy) would be within the scope of copyright. This is incorrect legally afaik (IANAL), and a bad idea to use copyright this way.

My suggestion is: drop the ToU paragraph that gives a different license to TLDRLegal from contributors. If you're concerned to guide compliance for the uses covered by copyright for the content, you could explain it as an indication, as an example. I don't know, maybe like "note that for the content covered by CC-BY 3.0, a way to comply with its conditions is to attribute it the same way TLDRLegal does", as you note yourself.

 “On another note, it doesn't specify which CC-BY. For a site dedicated to licensing, it's unexpected.”
 It indeed does, actually! See below:
 Content explicitly licensed to you by TLDR under the Creative Commons Attribution 3.0 license (“CC-BY”) shall be governed by that license unless otherwise marked.
 The text of the CC BY license is found at
http://creativecommons.org/licenses/by/3.0/legalcode

This is for "content licensed to you by TLDR". It's not for content licensed by contributors to TLDR. Unless I'm missing it? Sorry if I do, the terms of use are quite cumbersome, with seemingly repetitive paragraphs. I find "3.0" only twice if I search the ToU text, and none is about the license the license from contributors (to TLDR if that makes sense, or generally).

 “"You may not make, sell, offer for sale, modify, reproduce, display, publicly perform, import, distribute, retransmit or otherwise use the Content in any way, unless expressly permitted to do so by TLDR." - so tldrlegal wants contributions under a "CC-BY" which is stripping authors from the "BY", then turn around and use their work in order to disallow them and everyone else from the core rights of a sharing license.”
 So this is the catch-all statement listed at the beginning of the terms, and then we continue to “expressly permit” cases where you can do so. Naturally we must enforce a license on all contributions and give TLDRLegal freedom to use them.
 However, I think explicitly requiring credit to when a contributor’s content is practically used makes a lot of sense.  After reading your comment, I looked up the Wikipedia ToS and got a couple of ideas from there.  How they do it is along the lines of “if you use the full text, give credit like how we give credit”.  These terms you see now were advised to me by an attorney in order to protect me as I built TLDRLegal as a free resource.  While it does a good job at that, maybe it can do more for contributors? 

Well, I think the previous comment applies here too... Let me put it this way: if contributors license their work to the world as CC-BY 3.0, then TLDRLegal ALSO receives it. This is always true. It's an open license, so it's offered to everyone, including TLDRLegal by simply the simple application of the license by the copyright holders to their content.

Therefore, if perhaps TLDRLegal needed something, some rights, before this was true, it no longer needs them. It has freedom to use content licensed CC-BY, so other terms you drafted in the past are superfluous at best.