Yes, you will want to keep track of your personal Contributions and Distributions and having a personal bank account and business bank account is one way to do this as @Michael Plaks mentioned. 

We know that a dual fuel system would be more optimal, but the cost of running a gas line and venting is likely higher than adding another circuit for the heat strip.Furthermore, we are looking for recommendations for an HVAC installer in Chicago.

Another way she could have phrased things is ‘I realized I had to file bankruptcy, and I caught a huge break because it turned out that all my debt was forgiven, allowing me to begin saving and get on a better track earlier than I anticipated.

I think you are on the right track comparing options - however I would note that there isn't really a differentiation between "DCSR" and "ARM" - there are a lot of 5 Year ARM options for DSCR Loans so theres overlap - maybe you are referring to a true 5-year balloon bank/credit union type loan?

I insure my rentals with a commercial broker, Mark Roland with Four Square Insurance , that shops many carriers and tracks trends, etc.

where I failed in my business is not having a 1, 5, 10 yr plan and failing to see the assorted train wrecks coming down the track. 

The agents I know that close a lot, often times become a dual agent in the transaction or already have an agent with a buyer lined up. 

If entities are disregarded, you can keep up with more than 1 in a single QBO account using the location/business feature to keep track of them separately.

And how did you track the payments?

I like doing this because I know the listing agent can be more cooperative at times if they can do dual agency.