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!

Sounds like you're maximizing your income the best you can with the house hacking! Good job on working the bad debt angle; that will help a lot.

At this point going forward, you need to keep good records of what that income is so when you speak with a lender you will have that backup. Usually the lenders want to see a couple of years of tax returns in order to see your income history. Try contacting a few mortgage brokers and explain where you are and if they can help. I was working overseas for a construction company and didn't have the standard W-2 forms, but the broker had worked with someone in my position and had connections to make the mortgage happen. That being said, I'm sure there is a broker out there who can give you more details on their minimum requirements (i.e. documentation) to answer your question better.

That's great that you are paying down bad debt that should be priority number 1. Keep in mind that you will likely have to move into a new property to be able to use your VA loan, when you do so depending on your local regulations you could lose quite a bit of your current rental income because you would either sell your current property or likely rent out the entire property on a monthly basis.

Thanks for the replies! So far I have made my previous mortgage lender, she was great and knowledgeable with the VA process, aware that this is what I am wanting to do. Initially she said lets start the paperwork on pre-approval but i know that im not there yet back-debt wise for another month or two and she was okay with that. I also have a meeting later this week with a financial planner to make sure i'm tackling the debt in the best way possible.

I do know that I have to move into the new property in order for the VA loan to happen again, which is why i'm wanting at least a 3 if not 4 unit so it will still cover my costs. In the primary house i'm currently at, my full-time renter is on board to sign a 12 month lease, but that only covers about half of the mortgage, have you ever heard of a lender allowing the rest of the proof of income on an existing mortgage be from Airbnb rentals? I ask because I know the market value for rentals would most likely not cover my full mortgage on it.