So if you say got a 2-family in one of these towns, you could live in one side and then short- or mid-term rent the other side and max your income out there to pay down your mortgage.

When you break down the numbers by individual properties using the first purchased property as a templated for the additional properties purchased however, you will notice that the numbers being used in the example are not scaling correctly.It took me some time to figure out why the numbers were not scaling and adding up correctly but I finally believe I at least partially figured out why the numbers didn’t add up.By the end of year 3 the 3 properties are owned for the following lengths of time and reflect the correct numbers associated with that length of ownership (loan balance, equity, property value, etc).Property A - owned 3 yearsProperty B - owned 1 yearProperty C - owned 0 years, it will be purchased at the start of year 4But by the end of year 4 the properties should reflect the following years of ownership with their respective numbers associated with the years of ownership (loan balance, equity, property value, etc).Property A - owned 4 yearsProperty B - owned 2 yearsProperty C - owned 1 yearHowever the summary total numbers that were provided in the book for all 3 properties at the end of year 4 did not add up correctly.

Anyways, airbnb is still pretty profitable down in South Florida.

The existing business would be wound-down by the current owners.  

@Mason GriffinStarting with a duplex and using a VA loan is a wise decision for first-time homeowners since they often have cheaper interest rates and do not demand a down payment.

Once you narrow it down to properties like yours, look at the availability of those similar units.

When the market goes down, we buy even more of these houses.

Even if your deductible is $0, which is not, filing a claim will cost you more down the line. 

Alternatively, you could suggest an owner financing transaction where they become the bank on the property and this way they get to collect a monthly payment all while getting a chunk of cash up front (your down payment). 

Seems like safest play is be patient and safe for down payment, but curious how others got started if they weren’t able to do this.