If you have a mortgage on a property and sign another note, like a second, you can't subordinate the 1st, only the lender can do that. 6 1/2, a borrower who puts a requirement in a note for the lender to subordinate just trashed the entire LTV assessment, the borrower could put a lender in an unsecured position!

And with the new tax assessments going into affect, i don't even know if we will be making any profits this year at all...I'm very scared for those letters to arrive.

We have taken on portfolios that required multiple evictions with dozens of late paying tenants.  

The assessing municipality is required to use comparable sales and disregard the subject property's sales price.They take 1/2 the assessed value and call that the State Equalized Value.

@Tom SeccaficoThere are several dozen companies that specialize in some form of self-directed retirement plan programs.  

Our plan was to keep it for four to five years and assess the interest rate and decide to either sell or pay down the mortgage.

If you're not buying up to the maximum you can qualify for you should be fine.If you'd like to be in a ready position you could always get your credit, income, and assets reviewed and planned for in advance, because a loan is basically compromised of those three areas.LIke Chris mentions above though, if you buy a property that positively cash flows using the formula of 75% of gross income minus your mortgage payment per month (PITIA - principal/interest/tax/insurance/assessments)  = a positive number then "yes," your DTI will go down each time you buy another property.

Perhaps a General Contractor can come in for an repair "assessment" and can look for other damage related to the property, well, and septic tank, and give you some estimate advice.

My current agent is great and her family is full of investors and she has dozens of rental houses of her own, but I have to accept that her commission on my little $20k-$30k deals is barely going to keep the lights on in the office so I get worked in between other showings and contracts done at night but with Docusign that isn't such a big deal.

The current assessed value of the former building is ~$4 million; the assessed value of the property you seem to be looking at is $1.3 million.Don't get me wrong, this is a beautiful building in a historic location, I would just be extra sure to make sure the math and the comparables work out in your favor.