The neighborhood is ok but you have to be concerned about all of the taxes that will be going up in the city.

No i dont live there anymore but that does not mean that i cant relate and want to see the beauty in the city again.

We all start somewhere and the biggest hurdle for most folks is to get started.  

My biggest concern is that the premium price that it will cost and the associated financing doesn't leave much room for decreased rents or high vacancy.

I understand that there is minimum lot size to build a structure in Lee County / cities, so you would want to look into that as well, especially in Cape Coral as I heard that the lot sizes tend to be smaller there, and multiple lots would be needed to build a house there. 

The two biggest variables are condition of the condo to begin with (ie. if it is old, it's more likely going to have more maintenance issues) and the quality of the tenant that's in place.

So that part works for your dad.The biggest hurdle is going to be that the statutory order of a 1031 exchange is that you must sell before purchasing.  

Another crucial piece of this is knowing what's going on in your city/market as far as population growth, employment, industry etc.

I purchased both in city with an air-force base near by, with a strong demand for families to live in a home with a yard; also has the best school district around! 

I'm a family man and an architect living in Sunnyside, NY starting to research the market for real estate investment, maybe flipping houses could be a nice option due to my experience as an architect and designer.