There are brokers that do have good relationships with all the agency lenders and can help you navigate the waters. 

A few of mine include:Draining outside hoses, and bowling out any irrigationTesting sump pump and removing/draining any hose extensionsCleaning out gutters to avoid ice damsThermostat upgrade to a smart thermostat to conserve energyFurnace cleaning & check upFriendly reminder to tenants on snow removal responsibility :) What's on your list?

Also, I have been listening to the podcasts here and there but of course I think that's a little advance since I'm not entirely sure yet what they're talking about, however, they really make me excited for some reason and really pumps me every time I listen to them.

You don't want water getting behind the shower walls and rotting wood.  

By winterizing I actually meant draining the water supply lines and filling them with antifreeze.. vs redoing insulation in a crawl space.

It was almost sold, but one week ago, buyer's agent found our house full of water, because of toilet tank leaking during almost 10 days( we live already different state, and our agent worked on listing and selling our home).

I'm baffled by how a property's water bill is so high despite there appearing to be no leak.

However, he is currently paying way below market rent at $1400 (water and garbage included) for a two bedroom/ two bath/ and a garage in Everett, WA.

I would suggest if you're open to it, New Jersey, just over the water.

The original price was $180K, but we were able to negotiate down to $165K due to the roof age and some water issues in the basement (offered $170K due to roof, and went down additional $5K in inspection).