Situation:I am currently looking into buying a home that is 4,500 sq ft, but requires the entire house be renovated.

There will be little to no detailed records of expenses as this is quite an old-school landlord that is not willing to dive into the nitty gritty.

Do y'all require the tenant to have renter's insurance or leave that up to them?

My family bought SFRs in early 80's w mortgage rates >18%, but high inflation drove rents higher than debt expenses so they all cash flowedalso look at USFR, paying 5.37%, holds 8 week Tbill floating rate notes only, not as good obviously as buying Tbill directly at the top of the curve (i bought a 26weeker in late Sept at 5.6%) but much easier to transact, i suspect 10yr will fall over next 2 yrs (FED cycle) then slowly rise over next 30-35yrs (long us debt-deleveraging cycle)

While I'm not sure specifically if they or any companies that offer Damage Protection coverage for 2 - 6 month stays, I know some people require a security deposit for longer stays (sometimes only half month) to mitigate damage risk and sometimes renters insurance as well.

Heating oil is expensive and I only expect a 3 year period before I see a significant return on my outlay.

Flights are expensive, getting a big family there is tougher etc.

You have revenue (rent) and need to consider expenses to calculate cash flow. $5,000 Rent per month is great unless expenses are $10,000 per month.

That always assumes the deal meets my minimum investing requirements.  

If you're going to do Ellis Act, then you don't have to buy out either (but you will owe them certain moving expenses and time to move).