By Condo, do you mean a timeshare property, or a full time vacation property?
I can help a bit with the former.
We own 3 weeks of timeshare ownership, all in Orlando, all bought resale, for about $1000 total sunk costs (purchase price, real estate closing, and resort transfers). For those 3 weeks, we currently pay a bit over $1700 in annual maintenance fees (but MF's have been rising a lot lately).
So far we have not tried renting out; we use our weeks for ourselves or family or we exchange for other locations. Next year we may actually start renting as we haven't got enough vacation to use all of our weeks.
If you are considering a timeshare, you MUST start by researching. You really need to know what you want to buy, where you want to buy, and what the costs of ownership are. Luckily for you, there is another great online community over at the Timeshare User Groups forums
http://www.tugbbs.com/forums/ and their main site
http://www.tug2.net/ who will be more than happy to help you. I researched for about 4 months before I finally made the plunge.
As far as finding the right unit, there are tons of units available on eBay, but they are often the lower end units. The prime units in the best locations are often sold on other sites, or through realtors. There are a couple of realtors who specialize in timeshares, but you need to figure out where you want to buy before you contact them. All the information is easily found at the above mentioned site.
Good Luck
