So, I'm at a crossroads for deciding to buy or not... lots of context below and I welcome perspectives from those who've made some of these decisions ahead of me. I know these come up a lot and I've read a lot of old threads. Me: 49, married with kids, two good incomes, but we live in a very expensive area, good investments, a little cash poor because I have everything tied up in investments (building spec house to sell, rentals, 401k, etc). Private pilot with about 180 hours. I currently belong to a great equity based flying club with a few Cessna singles (172/182). What's changing: Well, I'm getting older, the kids are getting easier (we have activities, but "taking care of the kids" isn't really a job any more. I am pretty sure we'll buy a vacation/rental home in the next year. The vacation home is near an airport and is a 60-90 minute flight away (vs a 6+ hour drive). Flying: I really haven't flow much the last 2 years besides currency. Some has been my busyness, but some has been that when I wake up, and feel like going for a flight, the planes or booked. I've had other times where I have wanted to fly to a destination, but because I have to work around weather, I've driven so that I don't get the club plane stuck somewhere for a few extra days. I feel like if the plane didn't have to be back to anyone, I would "go" much more often, since both my wife and I could work remotely for a few days with no drama if we got stuck by weather someplace. I also feel like I would do a quick TFR/weather check on a Saturday morning and take the plane up for an hour, whereas now it seems too difficult or is booked. Bona fides: I have never maintained or owned a plane, and I guess I'm a little nervous about that. I don't have a ton of time to wrench on it myself, but can certainly do some things under supervision. The limiter would be more time available vs skill availalbe for helping the A&P maintain the plane. I expect my time to get more available over the next 24 months as i finish a couple of side real estate projects. I have restored a couple of obsolete trucks in the last two years, so I'm fairly decent at auto projects. Options: 1. Stay in the club. Pros: Cheapest, takes the least time from me. Cons: Only 4 seaters (I really do have multiple times a year where 6-7 seats would be amazing), and< i have the scheduling issues which are generally OK, but it makes anything spontaneous not really work. I suppose I could get my IR (and I likely will at some point) to improve dispatch. 50 hours a year is around $7,600 a year all in and I don't have to deal with any MX/etc. 2. Buy into a 6 seat partnership. I may be able to buy into a Cherokee 6 for say 25K. If this one doens't pan out, I could seek something like this (though they're rare). This would get me the capabilities I need in a relatively simple plane, with costs not all the much higher than what I pay now (a few thousand a year more). I would have more scheduling freedom, but would sitll have 3 other partners to work around. I think the plane and finances would be perfect, but worry that scheduling around people would continue to take the spontaneity out of it. The system the partnership uses is each partner gets 1 week per month, where they don't have to reserve it, they just fly it anytime during their week. If you want to fly during someone else's week, you just call and ask them. It seems like a nice system and the partners are pretty cordial. I estimate that all in, with 50 hours a year of use, this would cost me something like $13K/year. I'd be participating in ownership (not sure which "officer" I'd be), but I'd certainly get real experience with registration, maintenance, insurance, etc. 3. Buy what I *think* I really want. I have the opportunity to buy a plane that perfectly fits the mission for around 70k. I would have full availability with it, but would also be all alone by my little self to manage everything that goes with one of these flying antiques. I anticipate that this would cost me around 22,000/year to fly my 50 hours, all in with MX/Insurance/etc, but would go down after a couple of years as my insurance in retract goes down from that first brutal year or two. Pros: Sole availability, leave your stuff in the plane, take it as long as you like, and leave it somewhere if need be, never have to check with anyone. Cons: Besides the money, which is a real consideration for me (I can afford either, but 22k hits you in the stomach a bit), I guess I'm more concerned about being a babe in the woods. Maybe I'm too wound up about this, as I'm a smart, mechanically inclined person, who gets houses built, restores old trucks and does 100 other things. I'm confident that I could learn these things, and I have two to four experienced pilto owners (2 in type) that would act as mentors for me. (one of which is local and has local (ish) MX figures out with an experienced IA. I think the best compromise would be #2, but the best answer may actually be #3. Not just because I want it, but because #2 may not make it spontaneous enough that I actually use the silly thing all the time, if I'm still "checking" with people on availability, status of Mx, etc vs being accountable for all of it myself.