If so and they are shown as a loss, can those loss expenses counterbalance a part of the taxes I would need to pay due to the conversion from a traditional IRA to a ROTH IRA?

No different than owning a condo in a big building with an HOA.Its also possible that someone who owned a triplex did a condo conversion and made the three units into separate legal entities and created and HOA.  

Is there any difficulty in the conversion of that loan into a proper business format?

If you haven't yet- be sure to setup some "Keyword Alerts" to get into conversation in your target area.

There were in the process of an apartment condo conversion when the market dropped.  

Computer models also benefit from lots of tuning, machine learning, and if the company is good some really expert tweaks to take into account things newer folks would miss.Doing it manually is great because a person can sometimes easily see something that the computer model misses, and can take into account other things - conversations with owners, etc - that the computer model simply can't.Generally I find the computer models do better on cookie cutter deals, and people do better on unusual deals.

A "live for free" house hack might not translate into a good deal when fully rented and, conversely, a good rental might not provide cheap living for the year when I am occupying a unit. 

You should be tracking your response rate and your conversion rates.

@Tim Rothermel, the companies that service the notes keep detailed records of the conversations they have with delinquent borrowers.

People will always have something negative to say no matter what the topic; I find it best to pay no mind and only retain the aspiring or relative content of a conversation, if there is any.