IF you can supplement or eliminate your living expenses all together, your saving rate will go through the roof allowing you to buy that much more property. 

My recommendation is to find something where you can rent 1/3 or 1/2 of it right away so that you can supplement your income or decrease your negative cash flow to make your savings last the longest. 

She said it may be a couple weeks before she’s ready with all of the supplements and such with her insurance company.

Are you looking for monthly income to supplement your earned income?

Helping to place loans that can't fit conventional financing could help supplement your income.

Why not suggest she buys her own window AC units to supplement?  

I am getting a feeling this would be a mistake trying to rely on airbnb to possibly supplement my mortgage with how the economy looks.

We are a growing real estate investment company located in Metropolitan Detroit and are seeking an in-house property management professional to supplement our team. 

A good agent and property management will be crucial if you're investing out of state. if you like to use data to supplement your research, feel free to dm me.

Assuming this 20k isn't supplementing other cash that together would be enough to buy a good investment property:I'd dollar/cost average index funds while the stock market is falling, let it grow, then find another property.