I second what @Allan Bishop Jr. said: educate yourself, network, focus by narrowing down to a single niche and then take action by starting to invest.

If you have negative CF, and put up a higher DP to get a positive MCF, all  you've done is pay all your negative CF upfront. 

Stay positive guys!

Once you have a clear estimation of expenses associated with losing the current tenant, repairing/improving for a new tenant, leasing fee, vacancy/loss of rent, decide if you’re financially ready to initiate the action which will cause your current paying tenant to move?

They will likely want to see him move into and take title to the house in order to make that work.If you are only looking at multi units the best path I see/ know of based on your current position is a 15% down payment on a Fannie Mae conventional loan which will max out at 2 units.

Hey Jefferey, great job on taking action!

How should I be positioning myself financially before I start inquiring about the refi? 

Because you will have to get some good rent at that price to have positive cash flow.

My amazing girlfriend has been lucky enough to take an associate pastor position at a church in Richardson, TX.

For training in first position notes I learned through @Scott Carson - he and Eddie speed are the two largest I am familiar with.