Any charge that would eat up reserve funds would either come in the form of an invoice or go on a credit card to be expensed so I can't imagine needing "immediate" access to funds.Thanks for your thoughts!

Depending on your situation, I would either refinance and just eat the difference or sell and make a small profit and then move on to the next one.

Can someone help guide me in a direction where I dare say "have my cake and eat it too"?

The auctions here will eat you alive.

The big fish can't eat it if they can't see it, ya know? 

I’m standing in the open area we’re it’s a eat-in kitchen.

So in your buildout either concede something to fix the water/roof issue, eat into your profit, or ask for better deal.

If I plug in the higher tax and insurance rates based on a $280k value, it really eats into the NOI and cuts the value of the property by about $70k. 

I read real estate books, BP forums and listened to countless podcasts whenever I drive, eat, or workout.

(Im originally from Boston, went to college in Oklahoma, went back to Boston, then down to DC).I made choices while I was young to both live cheaply, and consciously chose to live in expensive areas cities.