From my experience: 250s don't depreciate much, so even a couple of years old 250 will be around $3K. 500s drop in value (but are still awesome starter bike).
So, I'd recommend looking for a 4-5 year old ex500 that most likely can be had for about $2K (Example: a couple of days ago I saw a 2003 500R with 49!!! miles for $3,500 Buy it Now price on Ebay... a girlfriend changed her mind on riding or smth. like that)
Well yall, I dunno how many of you actually check this thread still but I found a bike and I bought it about 3 weeks ago. It's an ex250, 2001. Really good starter, I'm short and I have to lower it a lil bit but I'm learning quickly, accidentally pulled my first wheelie the other day through some problems I was having with the clutch. Thanks for the advice from everyone in here and also thanks for coming by and letting me take a look at your bike John!
Yeah, and I was scurred shitless afterwards lol, but can't seem to do it again. I kinda want to, but the whole reason it happened was from people messin with my clutch and I don't want my clutch to be messed with now that it's somewhere comfortable for me.