That’s a decision you have to make. CFI may get hours quicker but is a lot more stressful is a lot more risk to your license and your life.

Not sure about that, depending on the 135 op, that could be more dangerous on both counts.

Piston twins launching over mountains at night in icing conditions....

Turbine power would make it safer.

I appreciate everyone's insight and advice.

The more I'm thinking about this, the more I'm leaning towards finding a decent sized 141 school with lots of flying and going the teaching route. Just power through it trying to get 90-100 hours a month and get it over with. I think this will better prep me for a regional than 1-2 years of reduced 135 flying.

Faster to a seniority number, yes. But I did enjoy teaching (especially my instrument students) and I think this would both be more enjoyable and better for my transition from the military to professional flying.

I lost four friends while flying old Barons carrying checks. Ever ask for a block altitude to the ground in ice?

GF

No, but I once asked for a block altitude down to 2000 feet below the MEA because of ice at night in the mountains. Don't understand the controllers reluctance to give it to me. Sure as hell nobody else wanted it. Fortunately I hit the freezing (or in this case melting) level only 1300 feet below the MEA. And yes, the aircraft was certified for flight into known icing conditions.