It’s a modest home, and we aim for broad appeal with a neutral, updated look that attracts a wide range of buyers.

Being that you already have property management experience and feel confident in your ability to manage a single-family or multifamily property, it really comes down to your financial position.If you have a good amount of cash available to put a down payment towards the purchase of a property and maintain sufficient cash reserves (or if you have a partner you can work with who does), then there's nothing wrong starting off with a multifamily property. 

There are a few temp fixes that still range in the $5000 range. 2. now add the furnace, garage door (not opener, but actual door mechanisms), front door that all will need to be replaced in next few years. 3. the gutters that need replaced now (ours are too small and its causing major overflow), and the flooring that needs replaced prior to renting it out. 

If  you are in the 20% range, you are better off going to the casino and putting all of your money on black and seeing what happnes.Since you are out of the area properly calculating cash on cash returns can be difficult because you have variable expenses to calculate. 

It's great that you're considering your options for attracting a broader range of tenants!

You are very likely to get in the range of $1,300-$1,400 if that is the market.

Obtain estimates for planned renovations and confirm if the allocated budget is sufficient.

However, that's not sufficient.

Quote from @Patricia Andriolo-Bull: If you don't mind non-waterfront, there are a few places in Marco Island around that price range.  

That will completely break my self-sufficiency test.