Too slow on pulling the trigger, so now I'm looking to buy one off of someone who cannot attend.

If you say you know you are overpaying, then why even pull the trigger and buy this? 

I'd just look for a deal that cash flows well and pull the trigger.

But it seems that because I received funds from the City / Landlord Mitigation Fund - which is set up to help landlords who house Section8 folks who trash their unit, or skip out on rent...that must have triggered something.

@Kedwin Allen Pull the trigger on it. 

I'd like to pay off the mortgage and really enjoy the cashflow but would this trigger a spike in how the house is taxed?

I would create a separate LLC for all properties and try to make sure a bank has no trouble with you transferring ownership to a LLC and it will not trigger a due on sale clause.

I have a good amount for a down-payment, but do not know if I should postpone buying my first property or pull the trigger?

Do connect with local investors, or better take a trip and walk the city yourself, before  pulling the trigger, as a deal may look good on paper, but be horrible in reality, a somewhat likely scenario if the deal is hanging out for any amount of time on the MLS in this hot market. 

If you have good credit and consistent income with at least two years of history you can definitely pull the trigger!