You will pay closing costs of XXX...and the person I am selling the house to will spend $20,000 fixing it up to sell it for $120,000, making a profit of $30,000 give or take depending on their financing and speed of the rehab. 

Or does that depend upon investor?

However I do know of a good looking triplex/duplex (depending on rehab) in New Smyrna Beach.

Depending on your specific location and amenities single families are renting for $1150 to $1450 in that area.How much equity do you have in your home?

The $850 price sounds about right - I see landlord policies as low as $500 and as high as $1500 per year depending on the underwriting details.

You can estimate between $43500 to $50000 for material & labor depending on the contractor.

For me it would really depend on the numbers for that property and what I intended to do with it later. 

What policy we used depends on the extent of your involvement. 

It all depends on your market.

That depends on state law, so it's a state specific issue.One thing they can probably do is fine the homeowner lots of bucks and make it cost prohibitive for the homeowner to rent to Airbnb.Then they can put a lien on the property and when they go to sell it, have fun negotiating with the HOA.