It is my understanding that the new owner will have the house at the cost basis of my purchase price, for calculating capital gains taxes or depreciation.For gift tax purposes for you - FMV.For capital gain tax purposes for the recipient - your original basis/purchase price 

Market insights and understanding the rental rates in the neighborhood.

However, understanding the passive activity loss limitations is crucial before making this investment.

I think if you are going to keep all three parties involved as owners of the deal long term then you need to separate yourself as a renter and a contractor.

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

i understand that's very general and each is a case by case basis; we've viewed a couple of them.

If I have a JV with other investors and we need to pursue legal actions, I always involve the other investors when interviewing attorneys.

What methods do other private money lenders use to pass along servicing fees to the investors involved?

I am starting with a small budget(100k-120k) so trying to understand which neighborhoods I should focus on, would love to get recommendations if you have :) I live south of the city and only like to go about 30 minutes away from home. 

Quote from @Brandon Stelling: Is there anyone who can help me understand how to leverage real estate investing being a military vet with 100% VA disability benifits?