JesseD
Line Up and Wait
Yes. My wife and my three boys (plus me). This is the situation I've been in since I got my cert. I fly a 182 right now and love the plane...in fact, it's all I really need right now...except for that extra pesky seat. It's affordable and carries a load of stuff...except for my whole family. It's a frustrating predicament to be in because as has been discussed, it's virtually impossible to rent for the situations where we all want to go somewhere. As it is, my flying has become somewhat niche because we can't really use it a great deal for quick family trips and the like because we always have to leave someone behind. My wife, while not "into" aviation, loves going places, and we would use aviation a lot more if I had access to 5 or 6 seats. Right now we do couple trips with friends or partial family trips...but it's certainly not ideal...and the travel aspect is what she digs about GA.
The costs of running out and buying a 6 seat airplane by myself are too severe, so co-ownership is my only real option, and it has proven quite difficult to find the two additional people that I would want to own with. Candidates come and go, and sometimes aren't as interested as they initially appear to be (or, as happened recently, find a really good deal on an old Debonair and pull the trigger solo).
I really wish that I only needed a 182. I would own one right now (I'm in a club, currently, but would love to own). As it stands, though, with my boys beginning to become teenagers and only getting bigger, I either need a big payload 6 seater, or I have to wait to buy something after at least one of my kids is off to college. I like the first option better, but it's proving to be very frustrating to try to make it happen.
I've snipped a lot here, but I'm just saying a couple of things.
1) Don't feel too bad, I'm stuck with the six seater too (wife, 2 kids, 2 dogs) and have pretty much decided on a Six or fixed 'Toga (depending on what's available at the time). Heck, if you were closer I'd probably be looking at the situation with you
2) Get your IFR. Every pilot I know says the insurance thing first. The real trick is what my CFI told me: IR requires more precision. You will, if you apply yourself to it diligently, make yourself a much safer (and insurable) pilot. My personal point on this is my dad. Always seems to be non-VFR when he wants to fly...