Or are there special title insurance companies that specifically insure these tax deed properties?

Just moved to Austin TX - Florida was getting expensive on residential side (tax reassessments, insurance hikes and mandatory flood insurance coming soon).

Currently, I do not own an investment property, and would like to own one in the near future and follow a buy and hold or house-hacking strategy (eventually transitioning to more multifamily).

This way, the seller gets 87k in hand, won't pay nearly as much taxes up front on a huge cash sale, will still be generating about the same amount of income as he is today, consistently for 20 years without the headache of managing it or insuring it.  

How do you all handle annual increases to adjust for taxes and potential insurance hikes and would you have them sign a new MTM agreement or add an addendum? 

Here is what I'm taking for reserves (outside of location specific expenses like home insurance, utilties, taxes etc.)- 10% for future property management -10% for vacancy-10% for CapEx-5% for repairs and maintenance-5% for lawn and grounds keeping-0.5% of purchase price for PMI based on my credit score For a house hack, is this too conservative?

Subsequently, employing the 1031 exchange strategy once the 27.5-year tax benefit deduction period has elapsed.- As I am not a finance expert, I urge you to conduct thorough due diligence in verifying this information.

Lastly, it's crucial to develop a clear strategy for your investment journey.

Moving forward, a better alternative than hassling yourself and your guests with damage deposits is to just purchase damage insurance through a company called Safely for each booking.

Basically if the interest, taxes and insurance (ITI) is equal to rents it qualifies instead of having to qualify rents against a full PITI (principal, Interest, taxes & Insurance).There are also some DSCR options that can use the STR like VRBO which tend to be much higher then the LTR - long term rents.