You'll get the benefit of their experience and you'll probably learn some ideas to incorporate into your plan. 

You must be a physic !

They typically want to have the person who physically served the notice and who works for you collecting the rent & interacts with the tenant so that they can testify.

You are correct that the tax treatment of Airbnb business (emphasis on "business") is distinct from other forms of real estate investment - and that you should get clarity about that to incorporate into tax planning and investment ROI analysis.

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).

Is it a carriage house as opposed to a garage, and/or is there enough room to incorporate another structure on site, namely, a 3-4 car 'modern' monstrosity?

Two common techniques I have incorporated with clients is to use a double corporation strategy or the utilization of a discretionary irrevocable trust.

@Joel Fine its funny you ran those numbers because i was doing the exact same this week as i was breaking down a market i saw as profitable until i incorporated the cost of a management fee.

If rent is not paid physically at a branch (i.e. it is paid online or via bank transfer), the date of payment will be considered the date when funds reach our account. 

A REIT on the other hand can fall substantially faster than your physical property.