The best thing to do for you is just to try, worst that can happen is they ignore you.   

Your projected time frame seems optimistic even for the "worst case".

Worst case scenario, you end up having to switch over to long term rental.

Even in the period from 2008-2010 (worst housing collapse ever) we saw a small correction of roughly 10% over the entire downturn.

The worst thing a wholesale buyer can do is ruin a closing.  

Same procedure for boiler/heating system but perform a separate test on this.Usually the elbows in runs near the exterior walls break first which actually reliefs other parts of system.I have seen freeze ups where it was only minor a few elbows here and there.It really needs to be done on a case by case basis but it seems like your preparedfor the worst but I don't think it will be that bad. 

I am in the process of purchasing my first home and would appreciate any guidance relating to knowing how to handle multiple-offer situations, what's a "good" worst case scenario, and if i'm blinded by rose colored glasses. 

It is in a midrange area, probably B to B-, maybe C+ at worst. 

From what I've seen, there's a large disparity between the best and worst sites, regarding how much oversight is done, due diligence, etc..

One of my worst fears is being scammed out of money by someone.