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

I would like to learn more but when I look up articles it mainly comparision of standard rentals vs air bnb. 

I also would return their deposit minus standard cleaning - why?

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?

It's similar to a credit card in the way that you start at $0, rather than the full amount a standard conventional loan represents.I would recommend speaking to the company you're receiving the HELOC from for their specific requirements. 

Anyone have a standard answer? 

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?

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