TL;DR (everything) but want to comment as a user not creator.
As a user I have generally licensed type before I needed it. I'm a little sick that way. As such I have a rather large library with far too many EULAs to keep memorized. When I go to design I do not first consider the EULA. Usually this is ok because none of my clients are huge. But recently, I ran across a problem where I was designing for a radio station in a large metro. However, the station is only streaming online (no DJs, all programmed) (no app, just browser) so really a rather small station. One of the designs chosen—as we were narrowing things down—used a font with just such a clause as you mentioned with the large volume (because online impressions). So then I started considering my options. I found another typeface but that license specifically required additional licensing for web use for a logo. A logo?
An aside, I absolutely understandadditional licensing for embedding in apps, books, web, etc. But for a logo I start to question my sanity.
Anyway so I went back to the first foundry—with whom I have a good relationship—explained the situation, and they told me we were cool. I stopped sweating bullets.
I license my type because it is the right thing to do. But I will generally backtrack and change fonts if I realize that the foundry is trying to—excuse me—nickel and dime me to death.
I have slowly been weeding my library over time to remove such fonts that I would probably keep using if it weren't for the EULA. And I don't generally suggest fonts—when people ask me to do so—from those foundries.
I think if a person wishes to share an image via Flickr so that they can get notes that is entirely up to them. But I think an official TypeDrawers group would have to be driven by other people. Personally I never enjoyed having to go elsewhere just to see an image when we were all on Typophile. I think it is better to keep images here and make notice that people are free to download the image and doodle on it if it helps.
FWIW It was not until I did that research that I really understood that the EULA is a document representing how foundries run their business and value their fonts and as such could never be boiled down to one simple EULA.
Even if a new spreadsheet were created today it would still have to contain many levels and asterisks to explain addendum and minutia of how a font can be used.
That said it would be totally useful if it were interactive and one could click on, say, "app embedding" & "basic license" and only a list of foundries that allow app embedding with their basic license were shown. In fact, I'd say without some kind of interactivity this spreadsheet would be only slightly less confusing that simply finding the fonts you like and then reading the EULA and contacting the foundry.