You are a high w2 earner, The house is worth 110k today, you are buying from your grandma for 60k in exchange for free rent for life, upside ARV of 200k.The costs of owning the house will help provide tax relief on your high w2 earnings, you are buying a great chunk of equity that will pay off in the future, and you and your grandma are doing each other solids. 

I really want to just relax and have a happy life and hope for the best.

These policies also cover you in all other areas of life like car accidents as well.

Sometimes life happens faster than you think (weddings, job changes, market shifts), so it helps to know your break even point in case you need to move on sooner rather than later.

You don't need to be larger than life, driving flashy cars, or using your looks to make a sale.

Well, Oregon can feel like an entirely different ball game.. especially if you’re used to simpler markets like Arizona or Texas.

Makes life way easier as tenants can't go complaining to you about it as its their own responsibility. 

I would talk first to an electrician as many do fire alarm and life safety.

You might want to get in touch with @Andrew Freed and Jonathan Bombaci, they are locked into several of the MA meetups which are great ways to connect with other investors in real life.

Consider putting the property up for sale and get your life back on track, then try investing again.