At the risk of trademark infringement - "Just do it!"
My journey into aviation was a mid-life crisis thing. After not passing the Air Force eye exam (20/40 in one eye 20/50 in the other, uncorrected.) I wrote off flying even though it had been a life-long dream. Fast forward the few dozen years and my wife and I are scuba diving at Walkers Key on the Bahamas. We walked around the aircraft on the ramp and my wife said, "You ought to look into this. We could fly ourselves out to go diving." When I got back, I found out that for GA, correctable to 20/40 was OK. I studied for the written, got a CFI to endorse me and took the written without ever sitting in a cockpit. The flying part went well and soon I was a Private Pilot.
One day at work a colleague came into my office. "You're a pilot aren't you?" I said yes and she said her next door neighbor wanted to sell his share of a Skyhawk. That night I told my wife, and she said, "You should look into it." After my heart started beating again, I was 1/3 owner.
Now I'm a CFI and still loving it.
I said all that to say this. Get started. Life will play out as it should and you never know how it's going to turn out.
Similar story here. Started differently.
Went to local four-year aviation college. Had three jobs to pay for it.
One of the jobs offered a real career shot. Took it. Had made it to Private Pilot but new job required extensive travel. Dropped out at 3 years. Very broke but no debt.
Fast forward a couple years, flying too expensive. Stopped. Again, no debt.
Wife and I ran up considerable debts for really dumb stuff for a few years early in married life. Paid it off over a very long time. Learned true meaning of "lost opportunity costs".
Six years later with a couple fits and starts, I'm renting sporadically, and generally unhappy with the mechanical state of the local rental "beaters" for the price.
I learn at a Christmas party that my dad's neighbor (at that time) was looking for a co-owner of an LLC that owns a 182. A sweet little old 182 with a STOL kit, sexy red paint, and zero squawks and ... later I learned, very clean history and logs.
Co-owners, wives, dad, friends... all conspire to convince me to stop saving money for a rainy day and do some living.
(You kinda build habits of not spending after traumatizing yourself with debts early in life.)
Had to rent a beat up 182 and when it went down for MX, the insurance company said the last few hours could be in an even more beat up 182RG (they considered them the same type, which from a flying perspective is laughable) to fill in the minimum 10 hours required to be added to the LLC's insurance.
Fretted, made spreadsheets, figured out how much a worst-case scenario of "engine replacement tomorrow" would hurt, fretted some more... and wife finally said, "What are you waiting for?"
Signed paperwork and haven't regretted it a single minute over the last three years.
Love my co-owners, love the airplane, love being back in avaiation. Couldn't have it any better. Well, a GPS would be nice, but we'll get there.
Flew the most hours in my logbook since the early 90s -- this year. Over 90 hours.
Last year did the hourly cost math. Winced and decided to ignore it. Hahaha. Too many intangibles as pluses of ownership to compare it too closely to local rentals. If I even ever think of selling all I'd have to do is rent a beater and I'd be cured of that thought.
If the co-ownership ever has to disband (everything ends eventually) I'll seriously consider a smaller aircraft and single ownership if I haven't worked hard enough to raise my income to a point where I could stay in a 182. Then I'd hunt for great co-owners again. The right people really make a difference.
Took me a couple years to warm up to going places with the bird. Took it to Arizona once, Vegas once, and two aborted trips to Oshkosh.
Learned that breaking down in North Platte NE just means handing the keys and your credit card to a mechanic and life goes on.
Working on the Instrument Rating now which has been a learning experience far beyond the items in the PTS, especially about oneself.
After that's done, I think a far-flung coastal trip is in order. I have an odd need to see an ocean every so often.
I'll find out how far away a long day's flying gets me in a 182. Kinda want to go see Jay's hotel down on the island. I'd also like to take the aircraft to the Wright Brothers memorial and airport and to Florida at least once. Key West would be nifty.
Also going to do more mountain flying. Love it up there. Different skillset.
Don't know about higher ratings. Maybe for the challenge. We'll see. Tying to push life into a corner doesn't work, I learned. If personal fiscal disaster awaits in aviation, oh well. Have eaten hot dogs and Mac and Cheese and PBJ before. Can do it again. Wife has always been more easy-going about stuff like that than I, so she'd get along too. Plus her career slowly keeps getting better too... Her first long-term management stint in healthcare started last year and she richly deserves it for her many years working her way up.
I joke with her that she's buying the next airplane, a TBM or Pilatus would suffice.