They usually deal with more "unique" financial situations for borrowers so its a potential their criteria will be different if you are looking for financing on a decent property.  

Does anyone have advice or a system that they use to help judge a strong comparable pricing structure for properties that are unique with hard to find the comps?

It also suffered frozen pipes & we subsequently flipped it lease to own to a contractor friend who has since done an amazing job restoring it.Bad winters have provided us with some very unique opportunities. 

I want my letter to be unique, but I also do not want to offend anyone by sending out a letter that says "need more cash for Christmas"?

You will run into at least a handful of them in your lifetime.Even more reason then for you to set up a unique avatar - when your name first popped up with this topic, I thought it might be that other guy at first, but his avatar wasn't next to the name so not him obviously.

If the item is older or unique they'll likely switch vendors... and that starts the 1 week at a time process all over again.But the worse case so far... 2 months to repair a dryer and they still can't get it right.

First of all, I didn't start this thread to attack the professional tradesmen, but sometimes it gets to a point where even if you want to pay someone for a job, you end up DIYing the last 10% (or 25 or 50) of the work whether it be additional damages, debris cleanup or poor workmanship.May be this is unique in South Florida, I am not sure.I have a long list of pet peeves, but I will just mention a few here that I noticed that seems to happen almost all the time.For example, whenever I hire someone to do work outside, say painting, stucco plastering, landscape, pest control, anything that involves borrowing your garden hose to dilute, mix, rinse...they ALWAYS find a way to deform the hose ends - by stepping on the connection, cross threading the connection, dropping the nozzle, clogging the nozzle, and they NEVER turn the hose bib off, they just release the nozzle handle and leave the hose pressurized. 

I understand the balance between time vs. money, but currently, I'm in a unique position where I have more time and can thus save more money! 

My broker's private bank and private lender options also denied it for being too unique of a property (it being an island) and had a concern about not having year-round emergency vehicle access (it's in Northern WI so we winterize it Oct-April). 

Every idea is unique and sometimes the way they work out don't make sense outside the context of that specific situation.