I am in my final steps and will be finding out if I’m cleared to close tomorrow.

What this does is cause the buyer to have to contact you to clear it up - which is when you tell them " $5K and I will go away, otherwise kick rocks!"

There is nothing wrong with either but it is important to be clear on your goal as otherwise you will likely fail at both.

Having a great relationship with an investor friendly title agent will make the process a lot easier for you among other things.If you find one in your area you can usually just call them up to speak to an agent or set up a meeting to talk in person and ask any questions you want about clearing title, the costs, timing, etc.

Rah-sheen try Clear Skies Title in Cranford.

I googled the owner and I believe I've found his LinkedIn but feel like a creep reaching out because CLEARLY I've just done a lot to find him...This is my first time doing this so maybe that is why I'm feeling this way?

You could factor in the turnover, collections and evictions, with some experience or at least some good assumptions -- but that would eat up whatever is left, I am sure.So yeah, probably need to just steer clear. 

You might consider having a conversation with your agent (and your attorney, should you ever need one) and make sure you both have clear expectations about who is going to make calls to whom, and for what. 

I feel like this would be pretty clear to the lender and could cause some problems.

There's usually a clear winner after you do this.Good Luck!