Offer the tenant a buyout having them pay the current month’s rent and the next month and return the security deposit.Are these my only  two options?

Quote from @Caroline Gerardo:Having a mortgage with a low rate is better than a free and clear property.

I'd be hesitant to break what is working on properties with a low base just to increase units..can/will rental rates increase on the currently owned units? 

Firstly, it has a relatively low cost of living and affordable real estate prices, allowing investors to purchase properties at a lower initial cost compared to many other cities.

I currently have two STR’s but am looking to grow in the future and want a software that will help me to grow and automate my accounting needs.

but the $7000 to pay off the vehicle will only save me about $600 in interest whereas investing that 7k into another home or renovations, like adding a new bathroom to my current 3bed 1bath home, would yield way more than the money saved.

I think a lot of this has come out due to the low standard of brokers out there that give the industry a bad name unfortunately... its so easy to get a license nowadays. 

You should be able to get a 75% loan against your current property.  

Currently making 50% plus on my ad spend. 

I expect MKE prices long term (10 years) to at least increase to the national average, there is really no reason why Milwaukee should not get there based on a current trajectory as well as infrastructure spending and re-development we are seeing downtown.We have seen consistent appreciation never below 6%, but also never over 8% over the last 9 years, which basically means median prices have doubled.