Insurance fell dramatically since a new roof was put on and I switched carriers. 

In December the roof was finally repaired, however the damage to the ceiling has not. 

Properties built with steel beams, both roofs less than 10 years, all heating systems under 5 years etc. 

From there mechanical and large items are my first priority (water heater, HVAC, roof) - though an inspection gives us more information and those items can be used as great negotiation tools during your due diligence period. 

It seems like there's an issue at least once a month that I must pay for, on top of trying to budget to fix several leaks (roof included), radiator not working, no shower in one unit, etc.

If you have a flat roof with drains, or a pitched roof with gutters I would ensure either way that the flow of water is un-obstructed most commonly by leaves or pine needles from trees.

I am from Spokane Washington, and the real estate prices there are through the roof and make it almost impossible for a new investor to get started.

There are short-term rental management companies that can help with that.One that I work with in Michigan covers the entire state and can advise on local short-term rental regulations or regulations that may be on the way, they can give you an analysis of the demand for short-term rentals in that area, nightly rates in that area, monthly occupancy percentage, and projected monthly income.They also let you choose the level of service you would like from them from full service to minimal.To your success!

if it's barely break even now... but needs 2 furnaces next year and a roof in 3 years and all new appliances now... that's not barely break even. 

My buy box is turnkey sfh 3/1 or small multi newer major utilities and roof.