Just to add my 2 agorot.
I once read an article about a couple who had bought a timeshare vacation home and ended up regretting it because they would rather have traveled to different areas instead of the same place each year (or a few times a year). Are you the type that likes traveling around or do you just want your peace an quiet?
Even then, if someone is planning to buy a vacation house they should either make sure that their neighbors are their type that they don't minding spending the next 5-10+ years being with them every vacation or not mind being alone to themselves.
If one has kids that should also be taken into account. Do you want to do the same attractions every year that are close by? How many times does Yossi want to got to Billy Bob's Barn Bonanza?