But 15% down, plus reserves, I think, is in the current Eligibility Matrix.

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?

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.

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

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.

Would love to hear your experience. and people have been telling me that it's currently about $150-180/sqft to build new so I don't know if it's financially viable for me to do it at this point.

None of the very small handful of students I have spoken with that are currently partnering with Ryan and Tyler on deals are happy with them and feel like Ryan and Tyler only have their own best interest at heart and don’t really care about their student’s success beyond lip-service.

I currently own two properties, one of them is cash flowing nicely in Arizona. 

I don't know how you are saving money when you account for your travel and time on multiple days, plus the stress caused by your upset tenant.2.