If you have one abuser, it won't affect everyone else systems.One thing not mentioned that could possible be a concern is were they are placed. ie. are they all positioned well for inspection and/or replacement if need be?

You have hit ALL of the areas of concern that I have with using my account for buy and hold or fix & flips.

I’m not terribly concerned about the house since the layout would make it easy to survey & subdivide to make it two parcels.

I do get you having some concern maybe going into winter in WI and wondering if tenant activity will be there to fill a vacancy (with lots of leases and moving around happening spring-summer).  

If cash flow is a concern it's a big one usually 

Is it possible for us to form an LLC and 1031 these into one 1.5 million dollar property in Oregon so long as we abide by the timing guidelines concerning the exchange. 

My concerns with them would be:1.

I can get you booked for a demo call to answer any questions or concerns you have and we'll tell you honestly if we're not the right solution for you.

I typically use regional banks to fund my deals but my 2 go-to banks have either slowed or fully stopped investment loans so recently I've connected with several online brokers but all came from ads or they reached out to me vs personal recommendations and intros so I have concerns. 

What has been your biggest concern about navigating these regulations?