but there lies my biggest concern, while I am investing in areas that I believe are going to appreciate dramatically as that is where some real money is to be made, I am buying to cash flow and not guaranteeing to myself or to anyone that the appreciation will really happen.

The money you save in the long run will end up boosting your NOI, which in turn boosts your property value.

We'll see how things are when I get there but I have a long way to go but real estate has certainly boosted my net worth and should help me retire early.  

An ounce of prevention is better than a pound of cure.Inspectors can vary DRAMATICALLY in their experience levels, and their thoroughness, and even the best inspectors will occasionally miss important issues (nobody's perfect).Therefore, each time I buy a property, I don't use one home inspector, I use SEVERAL layers of inspection done by SEVERAL pros.Yes, I use a regular home inspector, but I also have an experienced plumber scope the sewer line on EVERY property before I buy.

There are too many variables like the possibility that rent rates will increase dramatically or the tenant will turn out to be bad and you will need to get rid of them.

Find a local agent, property manager and/or boots on the ground since values can change dramatically from one area to the next. 

Additionally, I am aware that once I move out, I can list the home on VRBO and several other platforms to help boost bookings.The reason why I'm considering/leaning toward selling the house, is that when I begin to run the numbers, the expenses exceed what I could potentially make.

There are companies that have recently entered the market that do a full service marketing like GOSRT and MARKET MYSTR and others that provide templates and help but you have to actually do some work like STRDIGITAL and BOOSTLY.

You can lose a TON of money, or dramatically decrease your earnings, if you don't know how to manage the property well.

I’ve sold my primary before and rented for 4 months and boosted my bank account significantly.