If they were separately metered, each tenant would pay the $116.50 base fees and their individual use, which would be 3x higher than what they pay when sharing a meter.There are many options, but don't make it more complicated than it needs to be.

Individual deals for flipping will always exist, but there are certainly far less out there now than there were 3-5 years ago.

The transaction creates a realized gain/loss so you have capital gains and depreciation recapture to worry about a it relates to your cost basis.You couldn't even 1031 them "together" since you have to buy as much as you sold.What are you proposing that is a "little bit different?"

MTR was our initial strategy, but Furnished Finder has been a bust for us (renting individual rooms in Memphis, TN).

Ultimately, the decision comes down to individual circumstances and preferences.

Look at this mess YOU created, and lost income because your emotions are involved. 

If you waive the late fee, it will create more problems in the future. 

I wanted to create a checklist of potential major problems to look out for when considering older properties (pre-1960 build), especially regarding deferred capital expenditures. 

I am part of a group of 4 individuals who want to start flipping houses.

I am trying to create a roadmap to get here and I am struggling.