Any ideas for systems that could alleviate this?

Wow such faster results and higher success and less failure; however the mentor will help you alleviate are some of those painful lessons along the journey.So what would I do in your situation?

So, now I'm confused at the timeline to obtain insurance and getting property management for my first property that I will househack in.Honestly, I was told o should get a PM since I'm green with rehab and to alleviate headaches.

Account Closed I would read into the local rules on Accessory Dwelling Units it may not be exactly your goal but a lot of cities with housing shortages allow ADUs aka In-law units to help alleviate housing shortages.  

I would attempt to find out what the sellers fears are and find a way to alleviate them with renegotiation.

I know its business but buying a property to immediately kick some one out does not seem like a good way to increase your reputation especially amongst the other tenants and would be an awkward conversation to have with that tenant.So how do you decide who gets to go and who gets to stay or are there any other avenues of approach to handle the situation that would help alleviate problems?

I will probably have to educate potential tenants to alleviate their fears. 

Alleviates the issues of going through the county records and trying to find addresses.

This would alleviate the issues above. 

It would seem that finding the right deal would alleviate some of the stress of the process.