My goal for the team would be to have one project under-way by EOY.The exit-strategy of each deal will be dependent on location, market data, and ROI comparisons to determine the best route forward for the team and our goals at the time.

Using a family address could expose you to unnecessary risks in the event of any legal or financial issues related to the business.Additionally, these virtual offices often provide extra services like mail and package handling, telephone answering services, and access to meeting rooms, making them a more professional and practical solution.

I do not see a need for extra cost or tech not all of your guests will appreciate (i.e. older generations).

Chris would tell him I hadn’t sent the money when Chris actually had gotten money for the rehab at closing, plus extra that I sent for change orders (which had not been done).

I'm struggling to generate extra lead flow from builders, mostly because it's so difficult to identify folks that are doing ground up, business purpose construction. 

With all this said, to answer your question of how you'd value this for a sale, I'd get a STR specific broker that's able to market your property as a turnkey STR with data on the rents, figures, etc.

Hopefully, based on actual field measurements, past project data, and estimating software, your contractor can develop a detailed estimate that lays out the cost of labor and all materials for each phase of the project.

Also, if anything were to go wrong I wouldnt have the capital available to pay extra on a property every month. 

The difference between MKE and Chicagoland does not warrant the extra effort that comes with going remote.Everything gets so much more complicated as soon as you can't swing by your property after work.

While state specific leases are simple and can work, spending the extra investment and having a real estate attorney help create one for you will likely create more value/protections and save you money in the long run