That roadmap, as of right now, is outlined.Learn - Keep FTJ (Full Time Job)Books, podcasts, BP, peopleFTJ and PTJ options: Go back into being a residential handyman and contractorWholesale - Keep FTJRamp up Wholesaling, possibly until either quitting or finding a PTJ to offset Wholesaling goal - raise capital to flip laterPlataeu Wholesaling, ramp up Flipping while ramping down WholesalingPlataeu Flipping, ramp up Buy-and-HoldLong Term Goal: rental portfolio with extra capital to invest in othersMy motivation does include swinging hammers (I love the physical work), but I recognize that won't be where I need to put myself to make money past the short-term (and my body won't be able to do that forever).

I have found a lot of good resources already in my short time here!

After flipping some 25 properties, I realized that buying and holding would probably build more wealth and cash flow, rather than paying those high short term taxes.

If so, what are some average annual premiums? 

Whereas I believe I could get between $100-125 per night for the place during the off season and potentially more during peak periods doing short-term Airbnb rentals.

I have gained substantial equity but don't want to pay capital gains and have been in the home for a short time (about a year).

Also, these are really short - I will probably just listen to them all while immobile :)  Thanks again.

as low as 5% down on 2-4 unit, lower mortgage insurance premium and no upfront insurance payment at closing, and it's a conventional loan so stronger offer and less red tape than the FHA. 

SF short term rental rules treat it as a separate unit, so you must rent for > 30 days for each reservation. 

I think it is short sighted to shingle over.