Positioning myself for first investment purchase

[Lester Nelson]

Currently I am house hacking my primary residence. I bought my house just before discovering the endless possibilities of real estate investing. I am now trying to get myself into a good position to secure a 2nd property, preferably a 3-4 unit multi. In order to do this, I have discovered I should still be able to use the VA home loan for an additional property because I only used about 1/3 of my entitlements on this first home.

To show that I am able to handle the multiple mortgages, I have rented out my basement to a full time roommate, and turned both of my upstairs bedrooms into Airbnb that are doing surprisingly well for the market in Cedar Rapids. I have a substantially sized shop for a backyard and have turned a room in it into my living quarters.  I also have a 42k/year full time job, army reserves that brings in approximately $250/month, and am starting a part-time job next week that should bring in about $750/month extra as well. 

I do have some bad debt that I am getting paid down in order to make sure my back-debt ratio is good to go as well. 

Is there anything else that I can do to help my chances? Also any recommendations on the house hacking front? Any feedback or pointers is greatly appreciated!

Thanks!