@Shahn SattarI’m not a tax professional, but I don’t think you can pay their heloc and write off the heloc interest on your taxes as an expense.Only way you could write off interest as an expense in this scenario is if you are actually paying your lender interest for the privilege of using their money (on top of the interest the heloc charges).

If that's the case, essentially, there are two types of professionals that can help you when investigating and analyzing the comparable sales in an area -- real estate agents and appraisers. 

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

You may want to even intern for a seasoned professional. 

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Determining this might be common sense, but I'm hoping some of the professionals could weigh in.

I wanted to use this forum to take the opportunity to find out from professionals how they keep track of Budgeting their money. 

For the locals in the area that might be able to help pinpoint areas of focus here --- think if you were an established hard working professional (not CEO or independently wealthy)  working at for example -- Redstone Arsenal, NASA, Military, one of the Universities or major Hospitals, the airport, a local lawyer, dentist, fireman, police, teacher, business manager, small business owner, corporate executive, etc, etc..  

Yours seems to be unique and definitely needs professional help.

You sound like a professional investor.