According to the Planning Board, the intent of the RM-2 Zone is to create, maintain, and enhance residential areas characterized by a mix of single family homes, duplexes, townhouses, small multi-unit buildings, and neighborhood businesses where appropriate.I'm assuming by definition I am zoned to convert to a triplex?

The parent must file a gift tax return annually, and any remaining balance is included in the estate.If the home was your primary residence for at least 2 of the last 5 years, you may exclude up to $250,000 ($500,000 if married filing jointly) of capital gains from taxes.

Let us use an example:Average 3/2 pool home in Pinellas County within 10 mins to the beach, $3000-3500 per month rent.

Other risks, the contractor walking off the job, a storm hitting and delaying the project for weeks, someone breaking into the home and stealing stuff (which happened just the other day to a client of mine), a squatter, or drunk driver driving into the house (happened a lot at my old job as a firefighter lol).

What @Anna Sagatelova said about Cleveland properties is also true in Akron. 90% of the housing stock in the city of Akron was built before 1970 and there are quite a number of really fine A++ older homes especially in west Akron.

For me I think it depends on how much money you have invested into the home and for how long?  

I would like to start close to home as I plan to self manage the rental side of it.

They have a bigger single family home and a tiny home on the property, but there close proximity and shared driveway present functional problems that are undesirable for guests. 

I have 16 homes in Rio Grande Valley that are RENTED for $1000 plus per month.

To save those costs, you might want to stick to some year build and older, for example, if you cannot do inspections on the properties that you are buying due to off-market deals or something else that is hindering you (all sellers I buy from do not want anyone in the home till we close).