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?

@Lincoln Tudor this seems more along the lines of working with a title company first to get the documentation correct and then you can worry about the financing!  

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

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.

Additionally we have cleaned the property and documented all.

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.  

As long as the documentation works and it appraises, it can be done. has to be cash to be done right away.If you buy with hard money, you'll have to probably 6 months to 12 months depending on the lender.

Read all the documents so you know and understand what you are signing.