Considering real estate investing either prior to or after this.

I rented a 4-bed house in Royal Oak, then got 3 roommates that I charged each 30% of the rent, so they covered most of my  rent.You can do the same if you buy a house:1) More rooms the better, if renting to fellow college students.2) Can YOU live in the basement?

You can easily do this on a spreadsheet, and it will take less time to track than finding and learning new software.

There is a great group of members on here to connect with.

Is this the best strategy?

Use your BAH and others BAH.  

Real- Estate  is a lot tougher game now because of technology now allowing buyers, sellers to access the market using the internet without using agents but  you do have hot areas that can support  more bodies .

I have found it is better to use a Broker if possible so they can shop companies, and shop every year vs using a captive agent that can typically only sell their company policies.While it is good to shop, not always good to go with the lowest possible provider on insurance. 

Just more complexity and costs, especially if you ever refinance.

A bit more information.