You need to set a budget for ownership for the first 5 years (buy in costs and 5 years of MFs), where you want to go, and then look at travel expenses to the various places. YOUR WIFE must be willing to do this leg work as well as you - this should be a choice & decision where you BOTH of you KNOW what you are getting into.
If your wife is NOT going to work with you, she will always be moving the target all over the place. Timeshares are NOT like accessorizing with pocketbooks - more like having another BABY.
So get to defining what, where, how often, size of unit, travel costs, style of the vacation (eating out vs cooking in), need that rental car EVERY trip?, etc.
Never assume your friends will pony up $$$ to travel with you (ha, ha ... my friends think I am rich & am treating them to a vacation) .. yes, free they will come for soup to nuts; paying for anything (ha, ha). Expect guests to start whining about something like a rainy day or the cost of eating out or sightseeing or parking ($40+ dollars a day at an urban resort). example: I had one 65yo friend do a "4yo style" melt down because he DROPPED/LOST his "off & on" ticket for the water taxi; I asked him, "What do you expect me to do? Give you my ticket?" His answer was a firm "YES!" After I handed him my ticket, he looked at me and asked what was I going to do? I said, take the public bus back to the resort & float in the pool (plus curse you out with the pool bartender & pound a couple of beers down). He said, "Okay" and off he went. Never offered me a penny for my $14 ticket or brought me dinner or asked if I enjoyed my afternoon. Mind you, we had ridden a mile on the water taxi (15 minutes) and he spent 4 hours without me, enjoying his afternoon boat ride.
