I'm quite not 100% on wether or not if I purchase my first investment property where I currently live (Virginia) (*which I will be*). should I also gain my license here since I'll have a property within Virginia.

Hey Dan, renting to a sober living operator can be a great idea.

The port of Puntarenas is lively.

Fannie Mae has a requirement that if you want to use the rental income from the non occupied units, that you MUST have a current housing expense which means you cannot live rent free.

Most bankers can run live pricing to help you make a final decision without having to have your credit pulled several times or fill out a dozen applications and submit docs!

Selling would likely trigger capital gains taxes (unless you lived in the property for two out of the last five years or use a 1031 exchange).

It was a small $$$ project but time consuming because that was something I DIY'd while living in the property. 

Since you are living in the property, you probably have developed relationships with an electrician, a plumber, and a general handyman, if you haven't reach out and meet a few now, while you are in the home, so that you can easily make a call or two when it will be necessary.

They can't assess all the subjective data like overall layout, view from the living room window, the dogs next door that bark all day, the width of doorways, size of individual rooms, quality of kitchen cabinets and appliances, etc.The best thing to do is study your market regularly.

If you are doing a live-in flip why not use that equity for a down payment with a refi or HELOC?