Actually we were at this point back in the early 90's. My mother passed away and left us some "fun" money as a result. My decisions were a boat, a '67 Chevy Chevelle that I always wanted, or an RV. Well, after considering my wants along with those of a family, I decided that an RV would be fun for everyone.
A boat limits you as to when and where you can use it. We lived in northern Michigan at the time and had plenty of lakes and Great Lakes around, but cold weather issues was certainly limiting. We didn't live on a lake so trailering it would be necessary and that would require having a vehicle large enought to pull it around.
The Chevelle was a bit of a pipedream. Nothing further needs to be said.
The travel trailer would allow the whole family some fun and entertainment. We had Chevy Astro Van that would pull a small TT. Plus, after the kids found that they'd rather do their thing my wife & I still had the RV to entertain ourselves. And now with a larger RV and retirement we're finding lots of things to do with our camper......throughout the year. Spent about 6 weeks in Florida last winter and will go back for a longer period this coming winter not to mention all the other events and trips we take over the year.