It has close to 100% occupancy according to several data sharing software I purchased access to.

It sounds like my goals will change as I continue to down this path as it has for many others but I've been thinking that my first goal will be to have enough cashflow to cover rent (if we decided to stick with apartment life and continue living in the city) or to cover the mortgage of our first permanent residence.I probably won't stop being a software developer but I do enjoy the prospect of having a strong enough cashflow to cover my family's needs if I were ever to be in a situation where I couldn't work anymore.

Many gurus try to sell software or programs that claim to bring you deals while you are sleeping.  

You need to confirm their pay pattern and find out if they are tenants that you would like to keep long-term before signing another Y2Y lease. 

At the time I was training for Robert Kiyosaki and had developed software that analyzed 278 markets across the country.  

A local PE that does this type of work regularly, probably has the analysis routines set up in spreadsheets or other software, templates set up in CAD and word processor, and knows what local inspections department will require.

My one complaint with with the REIA is that someone is pretty much always trying to sell you something e.g. a course, software, a (bad) deal, etc.

@Brittany Villamil  If you are looking for software, I would reccommend HouseFlippingSpreadsheet.

I want to pull the trigger after confirming rents and utility costs.

This is just my 2 cents but the military member receives base housing allowance like clockwork and it assigned on a contract for how ever many years (you may want to confirm how long he has left).