Conventional wisdom here (at least for your first purchase) is to buy into a resort or system that is within driving distance from your home and that you will use. You also want good trading ability for those times when you want to venture away from home. Watch your maintenance fees (they are forever)
I like the idea of a system or network of resorts, like Wyndham, Disney, Hilton etc. I dont have experience any of them except Wyndham. They have lots of nice properties in good locations. They are strongest east of the Mississippi, but they are in California, and Las Vegas too. The cost of entry is low, if you buy resale (ebay for example) and the maintenance fees are reasonable if you buy the right contract at the right resort. (Maintenance fees vary from resort to resort, and even among contracts within the same resortso watch this.
I bought into Wyndham because they have numerous resorts within a 12 hour drive from my home; the Beach, the Mountains to Orlando even an urban experience with New Orleans. They are one of the few timeshares near Washington DC, where my wife and I both have family and San Fran Cisco where my daughter and Grandkids live.
Wyndham points are cheap on ebay and if you dont make the same mistake I did on my first purchase you can get a contract with maintenance fees at around $5 per 1000 points (a 2 bedroom in Destin in the high season will be under 200000 points or about $1000 a year)
I subscribe to the theory that points are points and it dosent matter which resort you points are based at. You can almost always make a reservation where ever you want whenever you want as long as you can do some advance planning. The exceptions are weeks like bike week in Daytona, or Mardi Gras in New Orleans, or Christmas in Orlando etc. If you absolutely have to have a week like that buy your points at the resort in question so you will have Advanced reservation Priority.(13 months) (havingg said that i did get Mardi Gras Reservations at 10 months with my north carolina points)
Now re Pensacola: Wyndham has resorts in Destin (60 miles away) and Panama City (120 miles away)
Most of us wyndham owners have had good experiences at the resorts and with the Wyndham people we encounter on the phone making reservations. Even the folks at the transfer dept and financial services have been a pleasure to deal with.....But be aware the sales people at the resorts are dogs. They have the ability to ruin a vacation if you let them. They will invite you to owner updates which are nothing but high pressure sales meetings, They will say that there are problems with your account and insult you for having not purchased retail...you have to know how to say no or just not go to these meetings.
The Wyndham Owners directory with a discussion of all the ins and outs of the system is here:
Wyndham Directory Read through it and the discussions at the top of the Wyndham section here on TUG,and everything else here on tug, do the same for other systems and individual resorts. . You might also follow ebay to get a feel for pricing...Then decide
Good Luck
