From the fact sheet it's not clear to me if I would be able to evict both tenants or just one of them because it says you can take possession of only one dwelling unit and I am not sure if each of the studio rooms counts as a separate dwelling unit?

As the 3rd largest MSA in the country it's hard to generalize the Chicago market as it's actually over 100 different submarkets when counting the 78 communities in Chicago property and then adding in the various suburbs, including in and around Naperville. 

I use Appfolio for my property management company but I think they have a minimum door count of 200. 

I know in business that every dollar counts but is it worth it to burn a relationship? 

The size of the house is 3500 sqft, single story, and only a 4/3, and rather small at that BR/BA count for the neighborhood. 

I do have my VA disability as my "job" income and I hear that lenders will count that at 1.25% for calculating DTI since it's tax free.

What counts most in RE are relationships, and this is as easy as going to RE meetups and adding every day just 1 new contact in your CRM, and following up every other month.  

It was a gut punch to see the tenants whose income we were counting on mass exodus the building right after we closed Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

If I finance the rebuild then the 1031 exchange presents some challenges (I will need to land a property that cash flows or breakeven so that I can get the loan for my rebuild, or banks will count that debt against me).

If you use Podio as it's designed to be used, it will streamline every thing you do--from managing leads, managing projects, reducing your internal email count, to making your internal communications more efficient because conversations (which otherwise might happen in email) happen "in context" -- of the client record in your CRM, the project, or whatever it is that you are discussing.