You need to learn real estate before attempting to understand real estate financing or deal making.

Remind them that not all states require a landlord to make a reasonable attempt to find a new tenant when the current one wishes to break a lease (and unless the statutes have changed recently in your state Pennsylvania appears to be one state that does NOT require a landlord to do this);  however, if the TENANTS wish to put forth the effort to find a replacement tenant for themselves (passing your screening requirements of course) you will consider allowing them out of their lease.2.

This is where I struggle because after a few attempts so far I have been unable to remotely convince the seller of this being in their favor or being a good idea.

It will be critical to try and pass your test on 1st attempt because the certificate will the be good for 6 years verses 3.IMPORTANT,,,all certificates expire at deed transfer and the new owner has NO GUARATEE of future passing.

Matt Motil , I was doing some thinking about this as I was attempting to fall asleep.

in this instance) anytime over what could go wrong in an attempt to be too fast and reckless in the process. 

You should get several quotes and you will likely need to show them the plans so they know what you are attempting to do. 

I will also be moving out of my personal residence and into a new one later this fall and attempting to rent that one out as well.

This is what I've done when attempting to sell a rental and will do with a flip I'm working on.  

I was attempting to buy a SFH in Gary, IN a few weeks ago, and it was snatched up during the owner occupant exclusive period with HUD.