I'd expect decrease in values of RE located within a mile of a campus.

As rates have decreased you can see an uptick in seller financed notes.

They do not valuate ADU's based on a 2nd structure on the property (as of now), like a house & cottage or a duplex for example, so this does decrease the valuation.  

I'm cool with spending $300/mo to own this kind of asset, I just have to wrap my mind around my net worth increasing as my checking account decreases.

If the price is decreased by say $10k because the seller is not paying $10k buyers agent commission, then the buyer can borrow based on an amount $10k lower and must pay the $10k out of pocket.  

You could possibly decrease your 401k savings (which would increase your taxable income), and shift this savings over to your brokerage account. 

A real estate professional is a distinct designation from the IRS and there are certain rules/thresholds to do before you can call yourself a real estate professional for IRS purposes.You may want to factor in all of the above to see what the cost of cost seg will be and what your decreased tax liability will be for 2017 and what your refund will be from carrying back the NOL to 2016/2015.

At that point he would basically get his investment back that he originally put in, in trade for his monthly cash flow would decrease to pay back his 25% of the equity loan.

I plan to decrease from there as the dates get closer, if I'm not getting bookings.

It can certainly supplement and even decrease the length of your W2 employment making retirement attainable at an earlier age but very difficult to replace.