The only person who comes out ahead is the person who gives you the playbook and collects fees off of you. 

Personally, I started as a bird dog and then wholesaler in the single-family home business.

Online Rent Payment (please tell me you still don't collect rent in person).

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Please email me at my personal email if you have time to chat - need people in my area to offer guidance and suggestions.

Absolutely do contact Yonah, he is the best person to answer your cost seg questions.As far as determining feasibility, it is usually done by your tax accountant who can estimate your immediate and future tax savings.

How would you pay the person if this is part-time help?

@Bradley Elrod  if you  rent to a family member at below market rent it is considered personal use. 

The entry-level Quickbooks Online software itself is expensive $250/yr... that's not even adding up potential books/courses, CPA fees or personal tax filing software like Turbo Tax.

You need to seriously consider ditching this person and replacing them with a pro!