[DRDavenport]

Best place to stay is to rent a house with friends. Many of the rental houses are in Truman Annex (susie@keywestkey.com), which I find too inconvenient. Many have private pools, but with little privacy. Preferred Properties has more upscale homes for rent. A house rental for the week can run from $3,000 for a 2 bedroom to $10,000 for a 5 bedroom in a prime location.

You want to be close to Duval St, but not on it. La Concha is way too expensive, and the other places are dumps.
If you need a hotel, the Hyatt on Front St. is pretty convenient and reasonable (but not CO). Lighthouse Court is fine. The Gardens is a bit pricey, but well located.

Best bar to hang out is Captain Tony's on Greene St.
Best parties: Fetish night at Kelly's on Monday; the Fetish party at 801 Duval on Wed; and the Bourbon St Pub on Thurs. (You don't have to be really kinky for the fetish parties - just wear a bit of leather and have normal fun).

The Friday afternoon parade is relatively family friendly, and lots of fun.

The big parade Sat. night is more fun to walk in than watch (IMHO). If this is your first FF, pay the $100 or so per person for a decent viewing spot on Duval St., else get there really early. Or avoid the crowds on Duval St and head down to Southard St where the parade begins.

As far as having some fun exposing the wife, opportunities will abound. Just be careful on the street. Pubes must be covered in public. In the bars and parties, anything goes. Capt. Tony's little dungeon has been getting very busy.
Avoid "The Garden of Eden" (the nude bar on the roof at Caroline & Duval, above the Bull). If you so much as touch your wife's tits, security will be hassling you.

HTH