Another thing to be mindful of if you use a bank/commercial lender is the pre-payment penalty many include in their loans if you choose to refinance (many have descending penalties in years 1-5 that can start upwards of 4-5%).

The idea of being more passive sounded good but I was really apprehensive about putting in $100,000 and it being tied up for 5 to 7 years.

It's in a popular year-round tourist destination with a shortage of hotels and heavy restrictions on STRs. 

After 3 years of VRBO doing 50/50 splits for payments, I've run into 1 issue of no payment before checking and the guest promptly paid. 

In addition to a YTD paystub, we ask for last years W-2(s).

Assuming I could get ROI of 10% over 20 years investing in the market, what would you do?

We would like someplace family can visit 2x  a year and VRBO it the resto of the time as I should be able to have no mortgage on the property. 

Have them sign a lease (rent) and then sell them the right to purchase (own) after a 2 year period (priced at estimated appreciation).

People date for years and then all hell breaks loose when they get married and move in together.

We both occupied one unit for 2 out of the last 5 years.