@Seidy Lasker Wash sale rules apply to stock options if they are deemed "substantially identical" to a security sold at a loss within 30 days, such as options with similar expiration dates or strike prices.

What was their level of speed & competence? 

You don't know for sure exactly what their occupancy rates are but you can certainly get a feel for it by seeing what future dates are open.

Consider getting a statement signed by all parties which states that everyone has agreed to terminate the current lease early on X date and all obligations by all parties have been paid in full and that the deposit will be kept by the landlord and will be applied to the new lease. 

My number 1 tip would be to go off market and find owner that wants to sell at a discount / prefers speed and convenience. 

@Kevin Sobilo I was speed reading and wasn't actually looking for a perfect analog but your assessment doesn't sit well with me either. 

We asked the owner if we could start painting the house before the closing date...

Often that software will speed things up like crazy for you...might give you the equity number so you're only going after properties with X amount of equity. 

I don't think anyone has ever said anything about sheets, towels, Keurigs, wifi speed, tv stations, pack-n-plays, the games in the game room, the upgraded appliances, etc.

so I'm wondering if around $50k is reasonable to get a smaller single family home up to speed where it looks something like what you'd see on HGTV.