It’s functional but not pretty.

The tank to the fixer is functioning but needs to be replaced at some point soon.

Do I ask a contractor to come in and make recommendations and pricing on what needs to happen to have this property fully functional in the winter?

Other examples include a cracked window, wobbly handrail, uneven walkway, roof with < 5 years of life left, hot water vent/relief pipe not 18" from the floor - the list goes on and on.For conventional lending, they want to be sure all major systems are functional. 

I expect this is a function of building and material costs.

You can find properties in any declining market at a discount...but the question you can never truly answer with 100% accuracy is the value of the property after it has been stabilized...in order to buy at discount, you'll be looking at properties that need work...or that have some functional obsolescence...you have to create value by improving the condition.This is a more philosophical discussion, but you can buy anything at a discount from asking if your offer is accepted.

Basically is there a tool that has the same functionality as PropStream for example here in Canada?

Unfortunately getting outbid by other Buyers is a function of this Sellers Market. 

It's 2 older guys - they can be tough to schedule with if they're really busy on other jobs but they did good work for me.So do you have no off street parking at your place currently with the garage non-functional?

Take this rotation to fix your credit and get yourself right, then start looking at your next PCS cycle to purchase something you’ll live in, and rent out when you PCS again.