The general area goes from B to C, and some gated A neighborhoods, but the best investments are going to be the C properties in the B areas.The local schools are fairly consistent with what is available in surrounding cities such as Fort Myers and Cape Coral.

I've spent more time reading about HOW to lose this fat than putting in the effort to actually losing it, like going for a jog or consistently doing workouts/exercises.I just "jumped in" with renting out my bachelor pad and not knowing the true costs, I ended up selling that property because it was a financial dog, and putting it into a duplex.

The property is on San Juan Island in Friday Harbor. that is part of my hesitation, that any "boots on the ground" on that island is proving to be very difficult to get anything done everyone is on "island time" and are very expensive so the maintenance I feel will be my biggest headache.

I don't know those condos, but was considering a condo on Ana Maria Island a few months ago.

Let me know next time you're on the island and we can meet in person! 

For W2 base salary income, or hourly income that's consistently 40 hours/week, you are correct.For self employed persons, specifically, tax return income is typically what prevails. 

We have a property that consist of a house and a guest house.

There is no consistency and that’s good for you.It only means you must be clear about the issues that are important to you and search accordingly.

My portfolio consists of a retail strip center, a bank, and then various SFR, 4-Plex then a couple of other commercial properties.

If owning a couple of single family rentals do not rely on the cash flow to be steady or consistent.