We found out there is a HIP program which seems to be very good, with bonus such as signup bonus, holding fees, etc. 

you made two mistakes 1Renting out a condo 2Renting out a condo with an Hoa Bonus mistake : renting to two “ young guys” 

The main house is 2200 sq ft and it had a bonus room 800 sq ft above 4 car garage that has separate heating/ac.

De minimis does not apply until the property is in service - which is after the rehab, unless it was rentable and available before the rehab.Some items like light fixtures can be expensed right away via different law provisions (Sec. 179 or Bonus depreciation).

The transactional costs here are HIGH and my bet is the rent won't warrant all this exposure risk and low ROI

A Christmas Bonus must be earned.

Or if the show specifically says they "donated 6 months of free marketing," that was given by the marketing company because they received exposure from the show.

If the Service ever issues the technical correction that 100% bonus applies to Qualified Improvement Property (QIP) we'd have a second option for federal 'expensing' for non-residential real estate. 

He says ML is looking at mid 2020.During the next 18mo, he expects the market to continue to move up overall, but he'll be reducing client exposure to equities in anticipation of the downturn.

I get paid for my job, which is our agreement, and I'm thanked regularly which is my bonus.