Prioritize properties with strong rental potential and set aside reserves to handle unexpected costs.Finally, familiarize yourself with tenant laws in your target market, especially in Portland, and consult a real estate-savvy CPA for tax efficiency and legal considerations.

He was happy to allow me to rent out nightly because it actually helps keep his property in better shape than a long term renter (having a cleaner in there every turnover, short stay guests always let you know when something isn't working, etc) but didn't want to hassle with worrying about a percentage of income/management, etc.

Your accountant will need to know this as there is tax implications.

This is based on demographics/interests including age, profession, income etc.. 

I would say pay the taxes.  

It depends on non-SEC 8 market rents for similar properties, the utility estimate for your property, and the tenant's income.

If its a volunteer fire company you may be able to donate the house to them for the purpose of training and get a tax deduction .

I did find a CU that offers that product but they don't take into account the rental income from the other units.

These states impose a state tax on any realized gains from the sale of investment properties.

How long will they have to cover property taxes etc for the decision they make?