My girlfiend and I are looking in La Grange and Brookfield which is not quite as fast west as you, but my aunt lives in Wheaton so I am quite familiar with your area.What's your game plan over the next two years? 

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.

I think I went through 3 different people that were over my account because they would quit.

If this is simply you not wanting to accept partial payments and the rent is current, stop accepting it - and send a Lease Violation/Notice of Quit for Non-Payment of Rent - and force the full rent to be paid per the lease or start eviction.  

Btw, this kind of note-taking has been extremely helpful in other aspects of my life, and I imagine it will work quite well for real estate as well. 

It is the Most Hazardous way to buy real estate and not quite as easy as you state. 

It is pretty easy to keep it fully occupied but it does mean I turn away a ton of people who want a lease that doesn't quite fit my requirements. 

I manage quite a few properties in those markets.

It is quite rural and it is much easier to get a permit for these sorts of things if you even need one.

Without too much detail I had to quit my W2 job 2 years ago to care for my disabled son and my wife is still working.