i agree with tug - but go with the advice section first
http://www.tug2.net/tugadvic.shtml
www.tug2.net
everyone is different. but would get a nice timeshare close to where you live. especially if it one of the timeshares that allows you to use their facilties (recreation, pools, tennis, golf) when you are NOT staying there.
then check their maintence fees. once you know it, check the rental price for the week you want. It is very, very sad - but some timeshares will charge their owners more than the owner would pay as a renter.
so be sure and check this!!!
don't buy Orlando unless you are buying DVC. Orlando has high maintence fees and there are a bunch of timeshares in Orlando - so it is a fairly easy trade.
DVC is an exemption - DVC does not allow their holiday weeks to go to II most of the time (exceptions do happen). DVC controls their excess inventory - so it does NOT go to II. DVC never charges maintence fees higher than rental - if you own DVC long enough - it will be about 70% to 80% less than a rack rate rental from Disney.
DVC also controls their prices.
so the timeshares you can get for under $5,000 will never be Disney at 160 points.
now you can get a DVC trading through II with another timeshares - but most of the weeks will be in May, Sept, Oct, Nov, Jan - off season times.
it is rare to find a 2-bedroom for spring break or summer or the weeks before christmas.
don't think christmas to NY even goes to II.