It appears as though your first, and most impactful mistake, was the location you bought in.

What are the best ways to study and keep up with a certain market, in this case the real estate market, how does one keep up with all markets that can impact the real estate market that you are investing in?

I realize you did not write the lease and so you have no control over it, but you are now seeing how decisions in your lease impact you and the tenants during the lease. 

Determine the best you can what size impact on refinance that this would have on your refinancing goals (eg. $20k less, $50k, less etc.) and apply a reasonable rate of return that you would expect to make on that amount of money if you were to refinance.

Dropped out of law school after year 1, because I didn’t want to go into an intense amount of debt and law is not necessarily the way that I desire to make my impact on the world.

When you have a property that only cash flows so much, that has an impact on your return!

That's not investing...that's speculating, and THAT IS impacted by the economy.

Does anyone have general advice or info on how a HELOC might be impacted when it is opened when the market is high, but mostly operates during the down turn?  

In some areas and/or locations you will need an environmental review (statewide DEC or similar and/or local wetlands review or similar and/or review of any EPA-classed conditions and history).

I want to understand how these expenses will impact my overall income in 2019, and in the future if some of the costs are going to carry over?