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

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.

I personally have, and continue to thrive off of repeat investors but I am always looking to grow my network of relationships.So for all of my wholesalers and investors out there~Legitimate Wholesalers- have any of you experienced this dilemma and what has your solution been to establish legitimacy in a time where our profession is being too loosely equated to the "get rich quick" mentality rather thanInvestors-What are some of the pain points that you have run into with wholesalers?

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

For the new place, I think we would be looking at a short-term solution of 2-3 years before buying our "forever home."

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

Even though I don't have the answer for it now, I figured in a couple years I'd have a solution/better idea how to wipe out HELOC.Is it worth taking out this big of interest only HELOC to obtain another rental at this time?

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.