My concern is whether the city could deny permits for these modifications, such as removing walls or converting a garage, or if they are mainly just concerned with safety and habitability.

Amassing a lot of debt and being only able to make lateral moves if I sell is certainly a huge concern of mine. 

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. 

I'm concerned with two things which I will paste directly from the report.

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.