So, your focus may need to pivot from high rental cash flow to little to no cash flow as a rental with an appreciation upside.I would recommend taking your $150K to $200K and securing a solid equity position in something that will cover its expenses and maybe provide a small cash flow, but then is poised to appreciate nicely over the course of the next several years. 

Living in one unit and renting out the others allows you to deduct 75% of expenses like mortgage interest, property taxes, insurance, and shared repairs as rental expenses, while the remaining 25% applies to personal use.

Also, they ONLY earn the credits if their rent for months 2-4 is paid on time. 

I guess from an "all things being equal" framework, what are the variety of reasons that an older home are more expensive to insure than newer homes? 

But that is calculated after expenses and depreciation is factored in. 

At one point they fell behind by $2100 but has since caught up and paid me but did not pay the electric bill and it was turned off.

It's just one reason why turnovers are expensive.

A little about me for context: I live in a very expensive market in Rye,NY. 

Hello I am going to sell my primary residence in Idaho and use the proceeds to buy a less expensive home in Oregon without a mortgage loan (all cash).

You might also consider creative strategies, such as renting parts of the property to cover expenses while you navigate the process.Best of luck, and I’d love to hear how things progress.