Mike, real estate, like anything else, can be a miserable investment unless you are passionate about it.

So as to make the Failed A/C experience as much less miserable as possible (get it done quickly (depending on the season--at midnight if need be). 

Especially in WA state where laws are coming down the pipe to make being a landlord miserable and likely unprofitable. 

OR, they do too many different marketing techniques all at once and really fail miserably.

Well that is great, but the problem is, WHO actually shows you how to think differentlyI know a lot of people that make millions of dollars and they are freaking miserable, I would never trade my life with some of these people

Money just gives you the ability to have that.When we buy real estate we're buying four walls and a roof there's nothing that says that four walls and a roof is going to make us happy or feel accomplished as a matter of fact I know many people who go their whole lives trying to own as much real estate as they can only to finally realize they have millions of dollars and they're more miserable than they were when they were broke.Many of us focus on how to do things I think it's more important to figure out why we are doing something and understand what it is we want out of taking certain action and trying to realize what the end result is we want from doing any type of Action Real Estate included

So you may spend a lot more time looking for materials and spend more money on materials than many.As far as STR rentals are concerned....make sure you know the market and the sentiment of the neighbors...I would go knock on doors...talk to them....are they going to be supportive or make your life miserable.   

They can run like a well-oiled machine, they can make your life miserable, or they can destroy your property value.If the Board isn't acting, then you may need to join the Board yourself and whip it into shape.

If your friends won't do that and make you miserable, drop them - they are not good friends, and will hold you back.

Failed miserably and stretched myself for 2 years as it’s not my natural strength.