We focus on year leases and sometimes allow existing long term tenants to do shorter renewals if they're nearing the end of tenancy and moving or what not.   

The current owner is getting older and needs to move back home (according to family) towards my hometown.

Would be a great achievement if it works - I would also reach out to the railroad track company to ensure there won't be any disruptions or issues they may have when/if you start the development process. 

Do you recommend me buy a house to fix or buy another house new for me and use my current house for rent and move to the new one?

Unless the people were significantly value oriented (think super cheap) 95% of the time they would move on to another location over taking the double beds.

Went through the process (Notice to vacate, filing, etc).

I am trying to see if I can use a separate business bank account for each security deposit and avoid all the paperwork with W-9s.No need to suggest move-in fees - I am only interested in doing security deposits at the moment and am very familiar with Chicago RTLO.

I have never done a cost seg for any properties up to this point and understand the fundamentals of the process.

Im super well versed in the insurance side of things but not the investment property process -- i would love to connect with anyone who needs help with insurance and can help me start out too :) 

If something isn't working and one of the parties wants to move along, they should be free to do so unfettered.