I have access to 2 administration staff 7 days a week.

Ross Ellington , if the sum of your mortgage interest, any points, and property taxes exceed $6,300 for single filer or $12,600 married filing joint or $9,300 for head of household THEN you would elect to itemize your deductions and lower your taxable income by the sum of interest, points and tax.

I can lower my student loan payment because I'm paid ahead quite a bit. 

Have access to cash deals in the $100K - $150K range.

. $250k should be able to get you 4-6 SFH's in a good city, lower B class housing which would cash-flow well, each with 25% down. 

It's a beautiful city with good quality of life, and prices are much lower than the DC area. 

Then I would be only borrowing 42k and then paying the mortgage which would probably be a lower payment than the HML. 

(We went into contract at a price lower than their original asking price and their argument was they thought because we were purchasing it so low they I wasn't getting a commission?

If your accountant is familiar with Xero then at year end they can also access so accurate tax planning can be done before the clock ticks away at year end.

Is it not equity building, because if I purchase the house in future, I will be paying a lower price since owner will deduct the amount I paid to him.