I wish you well!

If you want to look at total expenses over the years, you need to look at total income received as well with your potential sale price. 

A tenant living in a 100 year old called board of health for drafting windows (never called us first) and BOH made us replace them within 30 days, well custom windows take longer than that to make so we got fined.

It happens with common names as well as less common names.

I'd look through the forums, reach out to a few and see who you connect well with.

Popular markets near us appear to be the hudson valley, adirondacks, finger lakes (although it seems STR's are under fire there), and even the cape cod area as we have vacationed there a lot and know the area fairly well.   

Quote from @Michael Eldridge: Switching tax preparer this year and since informing the previous one over a month ago they have been distant.

If the deal is in a good area, well taken care of, generates income, and will attract good tenants then i wouldnt worry about anything else.

Books related to "house hacking" will have information pertinent to what you are looking for. 

Stay informed and read plenty of books!