You'll need to ask the zoning office, but it's doubtful unless that's common in the area.

But because we can cash flow we feel it makes more sense currently to keep the property and sell within the next three years should we choose to do that and we'll still be able to avoid the capital gains and maybe even see more appreciation.We live in Portland, ME and we've been seeing steady growth in rental prices as well as continued appreciation for single family homes.

However, when the fundamentals of the underwriting do not make sense, that is more a reflection of the team than the deal itself.

I haven’t given any thoughts to the things you have mentioned but it has prompted me to go back to the drawing board to see what would make the most sense financially with my goals.

What are the most common home issues and repairs needed in [region, state] for houses built in [year]What are the costs to repair those issues?

I’ll worry about the rest after that.Regarding the 2nd property I mentioned, it’s not residential, so I guess theres no sense in doing much improving.

Basically you need to get yourself involved and throw yourself into the RE world I'm pretty involved socially with my business I just don't know where to find these "meet-ups" (that seems to be a common phrase) 

Most common treatment is to treat it like a business =self employment income and then take a huge loss against your ordinary income

Yes that makes sense, I do realize they aren't mutually exclusive.

Our house, in which I invested more than $150,000, purchased for $63,000, could be sold in February 2021 in that repair for $225,000 (which already made sense: if I sold - I would not lose anything, at least).