A lot of people get stuck in analysis paralysis, if you do the numbers, check them twice , three times over and they work pull the trigger, as a mentor once told me , "man the F up and put on your big boy pants" Knowing that I had done my research and ran the numbers and possibilities. 3) Understand that **** won't be perfect, but the pains and failures that you experience will give you life lessons that will determine if you want to continue or if this isn't right for you.

If I were to pull the trigger and buy a duplex/triplex, what comes next?

@David Knoll Did you end up pulling the trigger on an investment property in Jacksonville, NC?

But let me know if I'm wrong and whether or not to pull the trigger.

You guys might be a little quick on the trigger here;  in many, if not most, jurisdictions an owner can pull permits/function as a GC Only on an owner occupied property, not as an investor/flipper, and usually requires the owner to retain the home for at least a year before selling/renting, to qualify for that exemption.While the OP may indeed need a new accountant, he doesn't even know what kind of license the accountant was referring to, apparently he didn't even ask.

How often does this trigger the due on sale clause?

Current tax basis is approximately 25%-35% of FMV and the sale would trigger a sizable capital gain. 

This move will technically allow the bank to trigger this clause but supposedly they rarely do.

I might be a player and I work with a group of about 30-40 investors that can pull the trigger on this kind of thing.

(google FSBO scripts)Better to go a bit high than a bit low on an asking price (at least in this case)Pull the trigger on something you know you won’t lose to get the experience