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

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.

For your specific question about doing a JV on the loan, my suggestion would be that both go on the loan and then do a separate joint venture agreement...because you can not have an LLC on the loan for those loan types, they need to be in your personal names.I am not a lender so maybe one of my lender friends could chime on exactly this would work @Zack Karp, @Michael Facchini, or @Jose Valdovinos?

@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?

Are you noticing specific property types, neighborhoods, or price points where buyers are finding the most opportunities?

I just spent some time in your market, specifically out in Pasco county, and man is there some growth going on there locally! 

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

I will list some specific questions bellow.- If I use a 1031 Exchange, does the next property also have to be a duplex?

There is not chart, there is a website called Vyzer that tracks this if you are an investor and use their platform.I know this does not give you a specific answer of XYZ, but I hope this helpsPS:As a moderator I am not employed by BP but volunteer to moderate the posts to make sure they meet community guidelines. 

Do you have someone that manages it all including bookings and customer service or just specific parts like cleaning only?