Might as well start out doing as much value add as possible, right? 

In my scenario I think it's possible the landlord may come ahead. 

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

Even if you had to exceed that, as single you could convert an additional $485,050 above the $63,350 (or $503,350 if married) and you’d only be taxed at the 15% LTCG tax rate (not counting any state if applicable).Each year I’d get my taxable income as low as possible to give myself as much ‘room’ as possible in the 0% tax bracket and convert the max amount possible.

I would spend some time working on the formatting to make it as simple as possible to understand for a banker or buyer.

Quote from @Giacomo Matthew Degl'Innocenti: I very understand your speech but it's hard to believe the tenant has nowadays became invested of a far bigger responsibility than the landlord in making it possible to be having depicted an accurate profile also because is the landlord indeed who's on the business and receiving the money.Thanks your intervening here though  There is zero logic in any of this. 

There are a couple of $100K lots available, and I’m trying to think of alllll of the possibilities.

That said it is possible that you need to evaluate your stays and decide if it is worth taking shorter stays or sticking to some longer stays to reduce your time commitment and maximize the revenue for time invested.

Is a $300K profit on a flip possible ? 

An agent is ON YOUR SIDE as opposed to the wholesalers and investors you mention who are in it to make as MUCH AS POSSIBLE FOR THEMSELVES!