If I were to purchase 5 properties over 3 years for $200k each, which yield $1k each in monthly cashflow, I am essentially going into $1M of debt at the end of the 3 years to take home $5k a month.

@Luke Boff A home sale contingency is the easiest way from a paperwork standpoint, although it can be hard to get accepted in the current market.

@Dalton Cole Bodine This is essentially wholesaling.

Essentially the homeowners did not lower the price, but they agreed to fix the window issues after showing them and estimated the cost for all other repairs. 

We get paperwork and/or it is all listed online in a portal, each payment made and a breakdown of the tenant or address so the bookkeepers know how to apply the rent.  

If so, that would trigger depreciation recapture on the hot tub, which seems like it would essentially wipe out any benefit I had from taking accelerated depreciation, right?

Basically a short term rental is more management intensive (Your essentially in the hotel business) but potentially more profitable.

I am pretty confident the property would cash flow $100-200 after paying a PM (not dealing with renters) so essentially cash flow $ 0 - 100 if I factor in saving for repairs.

@Taylor Campbell Normally when someone borrows money to buy real estate, there is a mortgage (in some states this is called a deed of trust but essentially the same  thing) A mortgage is the document that makes the house security for the loan.

Most contractors won't want to do 203k work because there is more paperwork and they don't get paid till the end of the project.