You live there for 2 out of 5 years and sell tax free for 250k in gains free if single or 500k if married.Other option is 1031 exchange where you use a qualified intermediary to roll off your sale proceeds into another property.

We are looking to invest in a single family home that would serve as a vacation property in Florida. 

You might make the most popular push a single family rentals and they are just too risky. 

Because there are not too many multifamilies in the area, I'm currently looking to buy a 2 level single family house and build a second kitchen on the second floor, just like @Ron Gallagher recommended, but not in the basement, in the second floor.

LOI’s aren’t used with single family homes, no need for them and they serve no purpose on s sfh, just make an offer. 

They are interested in a lease option (rent to own) on a single famIly home.

Financial issues are possibly the single biggest issue the Military as a whole has to deal with that affects readiness. 

For single tenant net lease that is absolute NNN then yes an owner typically does nothing.For MTNL -multi tenant net lease then even though in many cases absolute NNN with base plus CAM you still gave to look out for CAM caps and large Capex expenses the owner would usually pay upfront and try to recover over time.For instance if you are buying a center looking at roof and parking lot are 2 big ones.

For those who do single family rentals, do you, as the Landlord pay for Pest Control?

Problem: Being that it’s a condo, I will be paying a HOA, but if I’m calculating correctly, there will be a decent positive cash flow.Thought Process: The lovely prices of single family or multi-family homes are a little out of reach right now, which is why I’m looking into a condo that I can afford.