Ideally, I'm looking at doing a renovation loan because I don't have the liquid cash to do renovations unless I drain most of my savings. 

what is the water piping, drains, electric, sewer and heating system condition?

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?

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

I work for a wholesale brokerage in Dallas and what I tell my investors to do is buy using Hard Money, fix it up, then refi right out of it into a traditional loan and get some of your money back that way you don't just completely drain your account.

I purchased a home recently and roughly two weeks after moving in my basement sewer drain had overflowed into my basement.

This is a very common problem in Parma: homes built in the 40's and 50's with downspouts and a driveway drain all running into a broken or clogged clay pipe that is flooding the basement. 

The floor plan was perfect where he could split the home in half, convert the laundry room into a small kitchenette (there's already a drain line for the sink and gas line for a small range) and he can significantly offset his mortgage.

He found several minor issues we expected but the MAJOR issue he found was that the 8 car garage addition ( 42ft x 42ft ) was build directly over the septic tank and drain field. 

I had a sewer line backup/clogged drain in my basement at my rental property in Harrisburg, PA.