As for the rest, there are major differences between Net Operating Income and Net Annual Income (or annual Cash Flow – which I consider the real measure of an investment performance, how much money puts in my pocket on a regular basis) and Cash on Cash Return on Investment.Net Operating Income is calculated before debt.Net Operating Income = Gross_Annual_Rent – (Vacancy + Operating_Expenses)Where Operating Expenses = Taxes + Insurance + Monthly HOA x 12 + Monthly Management Fee x 12 + Repairs and Incidentals (Warranty, Utilities if any paid by owner and/or during vacancy, CapEx reserves, etc., don’t forget the CPA and Lawyer costs) Again Net Operating Income is calculated before debt - what matters more is the NET Annual Income (or annual cash flow): NET Annual Income = Net_Operating_Income - Mortgage_PaymentsAnd that leads to the Cash on Cash Return on Investment: C/C ROI = Annual Cash Flow / (Down Payment + Closing Costs)And I’m willing to bet you don’t get C/C ROI above 10% on any SFR in Austin area (based on these calculations and bought with conventional means, not subject-to or assumptions, or owner financing or other creative financing).

Net income for the house after property tax and insurance is $500 per month. 

So future employment in this profession isn’t very stable.

Once you have removed the doubt of a previous owner wanting to get their property back by saying the county didn't handle things to the letter of the law, then you can get title insurance protecting your 100% ownership then sell like any other property.If you have a lot of old owners or bigger problems the the quit claim deeds from the people you can find will help speed up a Quiet Title Action.

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?

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