At that time we could renovate the ground floor apartment and potentially turn it into (2) apartments for a total of (5).My questions come down to how do we deal with the existing 40k mortgage, whether we can make it work so her parents aren't paying much in rent, if anything at all, and whether or not we set up any legal entity, like a trust to help the legal situation of paying off her sister down the road. 

Unless you had a foundation repair company you trust tell you needed a french drain.

Seems like such a waste but nobody can agree on a new portfolio manager as the old manager was a family friend for multiple generations and well trusted.

Since you’ve got a partner, an operating agreement is super important; trust me, I’ve seen friendships crumble over “handshake deals.”

He holds them in trust and cannot take ownership of them until a future event has occurred: A charge related to the tenants' leases for breach or excessive wear and tear, etc.No credit, no physical transfer, no closing.

If you want to be generating leads from a website, SEO will help with credibility and long term visibility, and an attractive website will also help with building credibility and trust too.

As others have mentioned - yes many folks use VAs that are great for the administrative tasks, but you NEED boots on the ground partners / professionals that you can trust in the coliving world. 

You need trusted "boots on the ground". 

I say take a gamble for anyone in which its even possibly feasible for and trust they're process. 

Please consider this if you move forward.Additionally, you need to have a broker on payroll in illinois and three separate bank accounts with the security deposit trust account located in illinois.