Have you thought about aircraft ownership? It's not cheap but I've found it fairly rewarding, especially considering I don't have to fill out paperwork but a flight plan whenever I want to depart IFR, which frankly isn't a great desire of mine. If I was single I could see a lot of nationwide destinations I would undertake without compromise. Though I would say, having a spouse or family to share on some of those trips with is even sweeter.

I'm a little surprised to hear a single 20-some year old without dependents making the homesteading argument. If you had reservations about the lifestyle of a commercial pilot as a single dude, brother those reservations are not going to go away when the wife and kids show up; they're going to be accentuated.

As to making a go at flying again, you're looking at having to find a benefactor, at least until you can make a bid for a mainline job. Even in this day and age, American women still act fairly entitled to the idea their husbands should make more than they do, and they're equally averse to the idea of bankrolling a man the way us men are expected to. So it's uphill for the regional guys. Intending to be a future head-of-household as as a regional FO or low-end 135 income pilot, without a well-to-do wife, is fairly irresponsible in my opinion, especially with an ATC job in the bag. Good luck whatever you decide. Feel free to PM me if you have any questions about piston aircraft ownership.