What search engines don't like is doorways that have exactly the same content, they see it is spam. Believe me, I know, I got busted for this from Google years ago, when I had the same link page on multiple domains and they banned about 75% of the domains.
If you do multiple doorways, however, and change up the text, graphics, etc. on each, it could be an advantage.
Lets say you are pushing big boobs make one doorway optimizing /big-boobs/, the next /big-tits/, the next /big-breasts/, etc and change the wording for each, maybe use a graphic that has the name changed for each, and move around the elements on your index page, so it doesn't look like they are all blatant doorways.
I think it is the long-term question, what are you trying to do. Get a lot of traffic off link lists (short or long term) or get less traffic and more from SE's?
I was in Beta Brigade years ago, one of the things they had us build was a "spider trap" where we built 40 different "pages" (or sites) where each was optimized for a different keyword phrase, and you interlink them all, then link to them from the index page. You named folders, images, pages, etc. with these keywords. It worked very well for me, I got a lot of sales off that one domain for about 3 months. (after awhile, if you don't update pages, you rank lower in SE's FYI)
I never submitted it to a LL, just to SE's. It took forever to build though, lol.
You could do the same thing with your freesites. Easy to change image names in ACDSee, and easy to search/replace those names in most html programs. It would be more work, you are not just slapping a new index page on your site, but the bottom line might improve in the long run when you site ranks for all those different keyword combos.
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