From what I’ve researched, I might be able to use my tax returns from the last two years to try to qualify but I’m technically not self employed.

LuThe midwest region offers healthy returns. 

To pay that amount in that town means the taxes triple, and makes the return on investment, not really worth it.

I also would return their deposit minus standard cleaning - why?

For example, if you see 3% appreciation, your paid-off property increases in value by $3k, your leveraged properties increase in value by $12k--quadrupling your Return on Equity (ROE).

@Jacob D AdamczakThere is no one right answer and a lot of other factors beyond just the simple one at hand come into play - age, other savings, goals, time you expect to be with this employer, etc.That company match paired with the tax deduction you get on your own contribution are essentially free and immediate return on investment. 

You depreciate up to your basis regardless of your entity type.If you are a single member LLC, then literally nothing changes on your tax return. 

The can also assess the rental rate and vacancy rate of the area (after you find a property)  If you are waiting for an agent to bring you properties, when they have other clients they are working with and other agents can easily see these listings too, they wont be the good deals.Good deals are found by networking, driving around, scouring the notice of default and foreclosure listings, etc.   

Find a market you like and BUY something that will provide decent returns and grow organically.

Remember a 1% appreciation in your property is actually multiple times more return for you depending on how much you put down.