Fender,
First of all welcome to the suck of aviation. You've been here a while obviously so I won't bore you with the nitty gritty.
I have recently spoken to several aviation consultants (for lack of a better term) and asked them about an upcoming pilot shortage. The 2 that I spoke with that pretty much know everyone who knows everyone simply asked me one question ... "Do you remember the pilot shortage that we experienced during '07-'08?". I said I did since I was hired in April of '07. The answer was simply this ... "The pilot shortage we are coming up on, depending on the price of oil to a certain extent, is going to make that look like nothing."
Take this for what it's worth. I don't have exact dates, but I can tell you that it's expected within the next 3-8 years. If you can get on with a "better" airline on the upswing of the hiring curve that would of course be the way to go. But you've been around this industry long enough to know what I'm talking about in that regard.
If you have the opportunity to own/run a small business and are happy where you are with the seniority you hold (QOL, pay, days off, etc.) taken into account, maybe stick around to see where the business goes?? If it takes off you could always buy a small plane and cruise around every so often. You may be one that doesn't want to work two jobs though.
It's a double edged sword as I like to call it. It could be great either way or it could suck either way. It will be a gamble for the business, but it will also be a gamble getting on with a better airline on the upswing too.
I'm sure I've been a lot of help ... not ... but that's just my take. I tried to cover both sides and give some info.
Cheers!