Sounds like the typical dilemma a lot of CFIs have when contemplating a move up the career ladder. The key here is to ask yourself what will ultimately make you (and your fiancee) happiest, and whether or not you're willing to wait for it.

When you described your current business (good pay, your own boss, etc.), that's a lot better deal than most regional hopefuls currently have. If lifestyle and income are more important, I'd recommend staying with your current gig. Life as a regional pilot can be a miserable existence, particularly during your probationary year. Additionally, with no prior turbine/jet experience, ground school, sim training and IOE will be challenging to say the least.

From what you've written, it looks like a regional gig is just a means to an end for you. With that said, I'd recommend holding onto your current gig and letting networking/word of mouth work in your favor. Your flight times are impressive, so someone is bound to be willing to offer you a gig in the right seat (even if it's just on dead legs initially).

Express your desire to all your industry (and non-industry) contacts. Nothing will probably happen immediately, but it's amazing what a little word of mouth can do. Hang in there a bit longer and I'm sure you'll be able to nail down a 135/91 job with persistence and determination.

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