Afterwards, the plan is to utilize my VA home loan to buy a multi-family property.

land flipping without entitlement plan is risky.

Greater Sarasota County allows 30+ rentals, but nothing shorter.Lakewood Ranch was "up and coming" in 2004 and is a great master planned community but probably is not ideal for STR as there is no natural draw. 

You can definitely get by cheaper here than in most metropolitan cities.Timothy Murphy IIIWill be in touch if I start considering that area, but for now plan on focusing on just Columbus.

Beyond that, if you plan on your properties to be property managed, you will be paying 10% of your gross income to the property manager.  

Depending on how you are planning to pay your friend  the profit out of the transaction.

I plan on holding my cabins for 30-40 years so I'm not worried about what happens over the next 18 months.

They planned on renting out the entire convent completely in a high rent area and use the proceeds to rent apartments for their residents.

Look into the reserves, see what major expenses they have planned for and what special assessments they've had in the last 5 years. 

But you can always ask the PM from time to time if they have experienced any problems with the tenant.2. expenses that exceed the pre-authorization threshold in your agreement.3. maintenance problems or concerns, especially ones that are not minor, but you can always ask about any problems, and they should be keeping record of maintenance problems during their management, even minor problems. 4. near expiration of lease term (e.g. 60 days), inquire what their plan in for a current tenancy, whether to terminate or renew.