You could actually make it to a regional in time to upgrade and still have maybe 15 years as a CA (assuming the current regional business model survives intact, which is unlikely). You could probably also get hired at a major in time to be an FO for ten years or so.

But the real question is do you want to make the financial and lifestyle sacrifices? You will never be able to to recoup your losses, since only widebody captains have lucrative income at most passenger airlines and you won't have time to get there.

Can you can maintain a decent income by consulting/freelance in your current field?

I would not consider it at all unless you have your retirement FULLY funded, house paid off, kid's college funded, and enough cash to supplement your lifestyle during the entry-level CFI and regional years...your wife will not think it's cool to live in a van down by the river (or the flight school parking lot).

There are trade-off's between 121, 135, and 91 employment...none is really much better than the other on average.