Good questions...

I will assume that you are a navy officer but not a winged aviator with fixed-wing time.

Fair to crappy regionals will hire you with slightly less than 1000 TT and 100 ME (maybe even less). Good regionals will often hire folks with 135 or 121 experience from not-so-good regionals. This can change fast however, so don't miss the boat while it's in port...historical hiring mins at the regionals have been as high as 2500-3500TT in the past

FAA ATP requirements are fairly low, but sometimes it's hard to get all the x-country as a CFI. I would not wait for ATP mins except make sure you have ther PIC, which should not be an issue anyway....when you get hired at a regional you will meet all the other mins in a few months. If for some reason you need an ATP while still a First Officer, you can just go do it out in town.

Most freight jobs could be considered stepping stones to the regionals. You could probably bypass freight in today's market. A very few guys stay in freight, upgrade to twin-turbine equipment, get their PIC and go to the majors from there. But night freight involves single-engine, recip, single-pilot, night, IMC, mountains, icing...get the picture? There is a real risk of death. Any regional is going to at least be safe, regardless of how crappy the pay or work environment.

The southwestern US (and FL) has weather that supports year-round GA flying. If you want to build time quickly as a CFI, go there.

You want to be at a career destination in 5 years...if you mean a good regional, you can probably be there in 2-3. If you mean a major, you will need to cfi your @ss off for a year, go to the crappiest turboprop commuter you can find with a 6-month upgrade, get the PIC, buy a 737 type, do the SWA interview, and hope you are in the lucky 20%.

Oh yeah, make sure your wife has a good job and plans on keeping it...worked for me