I know the IRS asks about entity vs personal members and if they're foreign or not specifically on the 1065 and other tax forms. 

@Gregory SchwartzWhat specifically are you hoping the software will do for you?

Separate the work into 3 separate categories: 1) Those that are specifically related to the future STR usage, 2) Those that benefit you while living in the house and have zero bearing on the future STR, 3) those that benefit both you and the future STR....assign a percentage to the usage.Be specific and complete.

Then ask them specifically if they help with this sort of thing.Oftentimes owners of businesses want their employees to "think like an owner."

Our pricing projections are based on market trends, historical data, and neighborhood-specific analysis.

It was a big alternative church property you know mind benders. one parcel in the middle of their campus 20 acres. they acquired from an owner sub too the back taxs and they never paid 1/2 of one years tax's prior to coming into title..

@Stuart Bartle - If you are interested in Chicago and looing for some boots on the ground and building you team...I am happy to make some connections with lenders, agents, contractors, etc.Do you have a specific area of Chicago that you are looking in?

Always keep in mind the alternative, the bank has no duty to sell for less than what the open market will bare for the asset.

There are also loans that are specifically designed for this type of property if there is enough work that needs done.  

ThanksArun, I am local to CT so happy to help answer any specific questions.