Assuming your goal is to rent as frequently as possible, you're going to have to establish your "team" in the area.

We do carry decent coverage and still get roofs replaced... you can buy cheaper policies for sure but by then you're increasing the self-insurance component and I don't choose to do that for a variety of reasons. 

He also frequently works up in Fernandina Beach.

I think you'll find a variety of opinions on this topic.

But FHA loans are designed to help the owner occupants own Single Family houses. 3-4 plex building are generally investment vehicles and have more deferred maintenance, these issues frequently get called out during appraisal.

We underwrite everything based on cash-flow ... never bank on appreciation, though reap the benefits of the forced variety where you can.

I personally haven't had a lot of success securing properties on these platforms for a variety of reasons.

Most of the properties are in rough shape and need a variety of work done. 

Agreed ... to add detail, project the future income and expenses (including appreciation and rent increases based on long term historical averages, sale if/when applicable, taxes, transaction fees, everything) under a variety of scenarios, then run IRR (excel function) on these projections to compute your rate of return ... the results will be enlightening and inform your optimal strategy.

Sub 1 million dollar properties tend to be of lower quality and in rural locations or if suburban they are more the mom and pop type variety and not national tenants.Step 3 Get with a commercial real estate broker to discuss if you want to invest in state or out of state and what kind of cash on cash you want to generate going in off of the purchase.Step 4 If you have no clue about want to invest in for commercial contact a commercial broker for step 1 and get on the phone so you can work through and find a direction you want to pursue with a commercial property.I specialize nationally as a commercial broker in retail and multifamily helping clients purchase.