I've done both this LTW and 20 simultaneous. With pre-mades. Ripp and Don. I didn't even use the cool shades for 20 simultaneous with Don (I'm playing Pleasantview without aspiration rewards this time). I did use the hacked phonebook and the teleporter shrub (for NPCs) to meet the townies, but after that, not cheats at all. Had to have Don retire to get it done on time. Ripp had college, so it was much easier. 20 woohoos is easier because you can then just have 10 loves and have a public and private woohoo for each. But then you have to make sure no other love interests are on the community lot.

I do it regularly and succeed, without ACR or mood adjusters (I do have a no jealousy unless steady/engaged/married hack though, which is very useful), usually whilst they are YAs or shortly thereafter.

I have a good number of sims in my hood, so it first starts with making a bunch of friends, starting when they are young. Chatting with other kids, bringing kids home from school, having parents invite over friends' families, etc. I can usually get a kid to have 5-10+ friends fairly easily. When they become teens, these friends turn romantic. Chemistry helps, but it's still easy enough to get a relationship high. If you have a teen woo-hoo mod (I do), then they can start young with their friends. Then it's off to college, which for many of my sims is a place of debauchery. Between classmates, dormies, professors, mascots, etc., etc., it's easy to add notches to the bedpost. And since YA's can woohoo adults and elders, you can go back to those family friends they've made before and turn them into lovers. I like my Sims having large circles of friends anyway, so it's not too hard to maintain 30+ friend/lovers with the occasional phone call (and most can be one-night stands, so you don't even have to maintain them if you'd prefer)

I have one romance sim who has literally woo-hoo'd everyone she knows who isn't (closely) related to her. I once had a frat boy who decided his goal was to woo-hoo as many as he could in Uni, I think I had him up to 30+, although he had to repeat a few semesters (with him, I'd work on building up a couple relationships at a time until they were high enough to woo-hoo, then move on... he was a louse

The want is easier if you have the sim be bi as well. Doubles the playing field.

Yes, I tried it and I probably would have finished it but.....well, just remember to always have backups of neighborhoods. I'm going to try it again, though, when I pick who I want for it

I tried it once in Pleasantview, where I created a female sim and made her a prostitute ^^" (I've always wanted to try something like that in my game and back then I played Pleasantview a lot and there were many teen, adult and elder males around ^^" ). I moved her in an apartment and ... started the 'business'. I, of course, used a mod (the 'easy bed' or something like that), because it would have been almost impossible for me to make 20 males fall for her and woohoo with her). I completed her want in ... 10 days or so (it was pretty easy with that mod). And then she got pregnant XD