When it comes to these types of auctions by the sheriff, is there a waiting period that must be observed before rehabbing/renting the building post winning the bid?

During this renovation period would you, as the lender, want an Actual Cash Value or Full Repair Cost policy in place?

The heating system, while straightforward, wasn't cheap for my 3 unit and will have a longer payback period. 

They then missed out on several more years of growth because they got out of the game and waited on the sidelines for things to look better. 2010 to 2012 was the period that cash investors were the players or those with IRA keep in mind investor loans were still basically non existent in those years for all those expect very well to do Investors beginners were not getting investor loans. 

Instead, I plan to rent during that period.

First tenant was on a fixed income as a retiree, so I was hesitant to increase the rent after the first lease period.

When a rental is taken out of service for personal use the accumulated depreciation goes away over a short period of time. 

Your decision to lease this property for short periods is what makes this a short term rental property, not the property itself.

(Interesting, because the best guess I’ve seen is that John maybe personally grossed no more than $10 million from this mentorship over a 8 - 9 year period of time).

Period.