Does anyone happen to know if there is anyone that can help or at least guide me to a person, place or thing lol that would have reputable training.

Pre-rental taxes can be an itemized personal deduction (Schedule A) if you don’t exceed the $10,000 state and local tax limit.Expenses incurred to get the property ready for rental, but before it is actually available for rent could be added under startup cost and can deduct up to$5,000 in the first year, if total start-up costs are $50,000 or less. 

Through coaching with Tom Krol, I learned how to get a deal under contract and sell to a cash buyer.

Since on of my wonderful BP colleagues already answered it above, I wanted to ask if this person would be open to re-investing the proceeds? 

Hey Paolo, I would say before partnering with anyone, I would figure out the person's strengths and weaknesses' before doing anything.

I am interested in learning more about creative financing for this opportunity.Best,YbC

If I ever plan to use a family member or friend who may not want to be fully involved in the process - what kind of documents would I need to provide that person that ensures their end is covered and could fully explain numbers, process, timeline, and security for them?

Its important to carve out personal outside space for each unit and make sure there is appropriate parking for both the primary home and ADU. 

It’ll position you to have more cash available for future investments.In terms of setting up a real estate business, forming an LLC could provide liability protection and allow you to keep personal and business finances separate.

They might look at the LLC mailing address to associate it with a person, but you could always use a Registered Agent and the address would be different.