I've seen excellent advice here. So, I figure I'd give this group a go - for my own situation.
What I have: We have 5600 points every other year. Very basic. All paid off. I know I overpaid with a cost of about 15K-20K which I am not happy about, but don't need to dwell on here. This is about moving forward.
How I got here: I was sold on the idea of "needing to use vacations" because we don't find the time to travel. With points to use, we would travel more. We have family that lives in different parts of the country - and for better or for worse, our limited weekends are usually visiting them. We hoped for some family vacations. and I was told I can always convert to hilton honors points for some of the shorter trips.
What I've learned: Our 5600 points barely get us a weekend - at some of the least desirable locations. We took one trip and they were basically apologetic - "well, its unfortunate you stayed there. that is one of our older locations." etc. In a few years, my kids will be in college or graduating - so, I do hope to have time to travel - maybe meeting kids at locations or just enjoying trips as a couple. (I have also learned that converting to hilton honors is a poor use of the points....or an expensive way to acquire them...its okay as a last resort, but not a good plan)
My options:
option 1) I've considered going "all in" by adding more points. This would allow us to take a decent vacation. I have an excellent contact that can sell us in-network hilton locations - it was advised by someone that holds a LOT of points to buy overseas because of the lower maintenance costs. for example, another 4K could get me 15,000 points...and I could at least get a "better" trip out of these points. Alternatively, I would welcome suggestions on how/where to acquire more points. My theory is that I may be able to increase usable points...and proportionately lower annual expenses. In 10-20 years, I can help offset that first fee by taking vacations (and my friend that loves these recommends some great places to stay)
option 2) cut my losses. If i get out now I will have taken 1 extremely expensive vacation. 20K + 3K in annual fees....and a lousy weekend at that. LOL. I feel like getting more points and using them wisely would be better. but perhaps that would be throwing "good money after bad", as they say.