Thanks for all the input everyone, definitely keep them coming, its helping me frame out my pro/con list.

I'm just starting to scratch the surface with corporate...but i'm seeing this as well. I personally know of a flight department (that reached out) and is seriously restructuring the way they retain/compensate. They historically wanted 3000 plus, with 1000 PIC, type rating, etc for FO's. Now it's Part 135 miniumums, they pay for type rating, "company health care," not "pilot health care", 401K match vests immediately, and profit sharing, vacation day one. Company pilots have the same company benefits package as the management team. Times are a changing.

Not to be a downer but. There was a reason you quit flying in
2015. Pay is better now but work rules really haven’t. How long were you at Colgan?
If you never upgraded your best bet is FO at any regional close to home and/or easy commute

I would hope that almost any decent regional these days has much better working conditions than Colgan. But that is a fair point... Most likely commuting will be involved, lots of time away from home, etc.

Commuting wasn't the issue then, it was the going out of business part that was coming. I was flying 135 when I finally stopped; I was tied to my phone with very few hard days off and my wife was very pregnant with our second child. Going to an airline then would have had me in training during her childbirth and staying with the operator I was with was no longer viable, so I took a break.

Now, short commuting is not really an issue, though a DC area base would be nice.

I was referring to a fractional over flying for a regional, and approaching the majors from a fractional. He already has 121 time. If the music stops, I would much rather have time built in with someone like Net jets than a regional. Frac's ain't that bad, may not be Delta or United, but if you get stuck and can't move on, they ain't a bad place to be.

Netjets furloughed a lot of guys during the last downturn. I was flying corporate at the time, and it was a VERY ugly time to be involved in business aviation. Not sure why you think it’s better...
It really isn’t.

I spent the majority of the lost decade at a regional and then finally bailed to a good part 91 corporate gig before going to the big 4. I’ve seen both sides.

The goal is to be at a major, so I’m thinking about the end of the career and working backwards.

Flying 250-300 a year in corporate, maybe some more at a charter or fractional vs. ridiculously quick upgrades (compared to 2000) at current regionals is something to consider when it comes to the speed of building a competitive resume.

I was flying corporate as well during 911, and 2008 and fortunate enough to still hold a good paying job. Bad times in business aviation indeed. Yes they furloughed 500 pilots and they were out on the street for a good 5 years before all of them were offered a recall. They were way overstaffed at the time and hired too many pilots, thats not the case now. Why do I think it's better? How about pay for starters ($82-60k a year to start depending on scd) plus overtime you don't even have to try for, all major medical insurance is 100% covered by the company(saves a family of 4 about $5-6k a year), 56 cents on the dollar 401k match(not many companies I know of offer this), home basing so no more commuting, perdiem you pretty much pocket because you get crew food (up to 4 meals a day). Keep all your hotel points, airline miles, and credit card miles. 2 weeks of vacation to start which translats to about 6 weeks of vac time on the 7 and 7 schedule. How about the Atlantic Bucks and fuel programs the pilots benefit from, which usually translates to a couple grand or more in gift card's a year. Tell me which regional will offer as much to start. Let's not even compare work rules and the strength of a regional union to that of Netjets.

The negative. Woefully slow upgrade times, loading bags (not really that bad), stocking the provisions and wiping down the interior, not many schedule's to choose from. Never know where you will be from day to day while on duty.

If I was looking to get back in, while applying to the majors I think l'd rather hang out at a good fractional then a regional. Guess it all depends on the individuals needs. Just offering another suggestion to the OP, as he wouldn't take near the hit pay and benefits as he would going to a regional.

I don't see why you think a regional is better.... it's really isn't.

I've done corporate, fractional, and regional. Still trying to get to the majors... hopefully soon! Benefits to all three, but still think the regional is worst in terms of pay and qol. The OP said he has 121 time and a family, so I was thinking maybe a fractional wouldn't be such a hit to pay and qol, and I've had friends hired by the majors from a frac, some with no 121 time. 100 ways to skin a cat I guess.