Probably starting out small Jaycee - SF or maybe some smaller duplex type properties.

But again, Chicago is a town where if you are one block over from the good area, you can go from an A to a C crossing the street.

I struggle to foresee a scenario where taxable beats MBD.

It started small, just helping to draft LOI's, running down property leads, making calls, but the important thing was just getting in and DOING it. 

I am considering the pros/cons of doing this without a property manager or real estate agent. 

I stuck to it and it has treated me well over the years.I did not start investing ( other than buying a home to live in) till many years later..

If you do it right, you can be very successful. 

I would just go on VRBO (or similar) and look how people design their properties where it really matters (they are trying to rent to daily guests and design/amenities are super important.

I do agree with a lot of the commenters here that pulling comps is the "easy" part, and everything that follows from there is where software could capture more value.

Your VA loan will be crucial to your real estate investing growth, especially since it affords you the potential opportunity to own more than one property, depending on your overall allotment.For active military personnel, that conundrum of where to invest and where you will end up is always part of the issue that sometimes causes analysis paralysis so it's great you have one in VA Beach already.