I don't know you or your situation, but why the focus on these high cost of living areas? If you do the regionals right, you'll be flying so much that you really won't be able to fully enjoy where you live anyway. You can string out your regional career for a decade plus or make short work of it in 2-3 years, that is entirely up to you and how much work you put in. For example, aiming for a gig with domiciles in Texas will give you cheaper rent and no state income taxes, and in most cases usually better seniority for things like holding a line and upgrading.

Save the high end coastal living for after you get to a major. Trust me, you don't want to live in Miami on less than 100k/year anyway.