We were just action oriented and even if we lost money, we treated these units as a mini pension, so when we pay off in next 20 years, it’ll just pay us a steady flow of income vs. us wasting money on consumer stuff since we are natural spenders. 

Would this contribution have to go into the expenses related to the purchase of the house, thus depreciated over 27.5 years, or would this be treated as a standard, deductible contribution, same as any other?

Most treat it more like a job than a business. 

Treat it like you're trying to wholesale the property.

I ignored this request yesterday because frankly it was unfair, she treats the other house mates differently and allows them to be negligent but for whatever reason she puts pressure on me.

If something's clean, people treat it better.Of course this is a case by case basis, but I've had clients who find the increased costs associated with renting by the room outweigh the increased income. 

I treat it like a game.

Just to name a few:  what chapter of bankruptcy, how the borrower is treating the mortgage/property in the bankruptcy, the location of the property, if the loan was delinquent at the time of bankruptcy filing, if there is equity in the property, the jurisdiction the bankruptcy was filed in, if the property is the borrower's primary residence. 

It may be a sole proprietorship, but you should still treat it as a business. 

Each of the properties acquired is now treated as a rental property on my client’s tax returns...resulting in all of the normal write-offs for those properties.