Stock picks. How we raised our kids. “Why was I still wearing bell bottoms in 1978?” We all have that list of things we wish we knew beforehand, or decisions for which we could have a do-over.

Timeshare ownership (or whether to buy in to begin with) is no more inoculated from 20/20 hindsight than any other (especially financial) decision. Ten plus years later, I hear myself gushing to non-owners about ownership, and sometimes still think, “Man, if I was listening to this guy in 2007 I’d be skeptical. It sounds too good to be true.”

I’ve met countless couples who express frustration at not getting the most out of their ownership, or who want to get out altogether. I continue to believe that a majority of the negative experiences are from lack of engagement in an ownership process which does require a time commitment to get the most out of it.

Ironically, perhaps, probably my top “wish” is not whether we should have become timeshare owners, but that we had done it sooner. Given how much we’ve traveled since 2008, I can only imagine how much more we’d have seen if we had started earlier.

Timeshare expenses can become a “thorn” and to that I have said in past blogs: It’s best to think of ownership like pre-paying for your vacations. I think (even in hindsight) that I knew this intuitively at the time of our first purchase, but it’s a point I don’t think can be over-stated.

Given that fees are split up and due partially in January and partially in July, the costs are spread out a bit – but to the extent possible I strongly recommend budgeting monthly – like any other ongoing financial commitment (a mortgage is probably the best analog). If your annual fees are $1,200, think of it more like “$100 a month.” Compare your timeshare expenses to the cost of full ownership of a second home, and timeshare is pretty reasonable.

I jumped into ownership management pretty aggressively from the start, but in discussions with other owners over the years I get a lot of “wow, I wish I had known that” reactions. To that point, I strongly recommend an aggressive management of your points. You own them. You’re paying for them. They do expire, so plan ahead and use them.

Many owners of fixed, recurring-week locations seem to think they have to keep going back to that same location. Our first purchase was a non-fixed, alternating year (odd/even) arrangement, so we didn’t have that issue early on. With our second and third purchases (2009 and 2018) we have fixed weeks.

Fixed weeks are points based just like any destination, and you can cancel (within the allowable period so you don’t forfeit anything), recapture the points, and use them to go somewhere else. In short, even if you love the fixed week location you own, don’t let it lull you into a rut.

I’ve mentioned this one before, too, but: get a Hilton Honors credit card and allow your purchases to convert to hotel points (HGV and RCI don’t always have availability where and/or when you want to go somewhere).

People hear “credit card” and think of the extra expense of monthly interest – a fair point. But I’ve solved this by incorporating my Hilton card into our regular monthly spending that I then pay off each month. Why not let your utilities and groceries and gas – and anything else you spend money on anyway – also fuel your vacationing?