If so, is this something that a third party servicer could do at my direction?

The reason is I know which lenders:- do a good job- stay on top of the necessary tasks- know how to be creative within the rules (some people don't fit into the standard mold of a buyer, and some lenders don't know how to get them approved, and some lenders know how to get them approved)- and which lenders can actually close deals.Another reason is, when someone wants to house hack, not all lenders are experienced in it.

Therefore, you can deduct items that are directly related(repairs) to the rental units plus items paid indirectly for the rental units(think real estate taxes, interest, insurance).in addition - it looks like you are looking to use parts of the personal residence as a home office.Just note that, it would be hard to prove that you use 100% of the personal residence as a home office. 

He will be selling the properties to me for about 35k each and they will rent for anywhere from $600 to $800 a month on a 12-15 year note with the bank.With his knowledge and history in this market I feel that my mentor is steering me on the right direction and not setting me up for failure.

Whether that be helping with rehab, direct mail, searching for properties, etc.

Did you know that you can use that and/or a Self Directed IRA to invest DIRECTLY in real estate?

Sellers are willing to get creative to make it happen as well so I'm trying to explore all possible avenues. 

A Heloc payment is usually 1.5% of outstanding balance due monthly I'm not sure how much exchanging one revolving debt for another with similar debt service is really going to help DTI. is this what a lender directly told you or is this what you are assuming?

Ask them what they are doing and how theyare doing it.I do some direct marketing and I always am networking with newer and more advanced investors.

They have me paying them directly instead of the old landlord now.