I don't love it because of the mortgage insurance if I put < 20%.

It's like insurance: would you pay every year a $1000 premium to insure your cellphone that cost $1000 and that you expect to keep 3 years?

With good insurance and good property management, the rest of risk should also be mitigated.So, what are you trying to protect and from what?

Do I need to get title and property insurance during the redemption period?

Yes, I'd like to avoid at all costs proceeding too far down the process if I am not interested.

I'm curious how you handle liability insurance in Boston.

B is likely referring to who between H/W would be entitled to most or all of the sales proceeds.

The homestead exemption has little to do with whether the property would fit in the 6 month or 2 year window for redemption .Most title companies these days will not issue title insurance until the 2 year window closes 

Her incentive to do this is that she'd rather loose $20,000 than the entire $66,000 she has in equity.Clearly, I need to verify the creditworthiness of the buyer, verify that they will in fact be able to refinance, verify they have strong homeowners insurance, walk the property, get title insurance, have lawyers draft the needed documents, and make sure it's all properly recorded and collateralized.

I'm planning to turn at least one of the 1/1's into a vacation rental which should earn at least 1200/mo (very conservative estimate, probably higher).Purchase price: 295,000Down payment: 25%, $73,750Loan term: 30 yearsInterest rate: 5.375%P&I: $1238.94/moClosing costs: $2800Gross scheduled income: currently $2650/mo, I'm planning on $3000/mo minimum with STR, so $36,000/yearLess Vacancy/Repairs: 10% = $3600*Gross Operating Income: $32,400Less taxes ($4700 (high estimate)), Insurance ($900), and Water/Sewer ($1800):  $7400Net Operating Income: $25,000Less Debt Service: $14,867Before Tax Cash Flow: $10,133CAP rate: 8.47%COC: 13.24%*yes, I know that's low for Vacancy/Repairs/CapEx, thats because we do our own work and management.