It was either this or go into health and wellness and become a personal trainer/coach/nutritionist as that fits my lifestyle and routine.  

If they're uncomfortable with helping you then they're either too busy or don't know enough about real estate investment property management to assist you.

Also, If you are hiring out most of the work you may be just as well off selling "as is" to someone who routinely flips and can do it cheaply.

You can do some work on the property, such as routine minor maintenance, but not value improving maintenance. 

Its sort of a good thing since they can be used when you sell to offset gains or in some cases the depreciation unrecapture.Talking of equity growth, here is a recent discussion that covers an important topic that is routinely glossed over in BP in favor of cash flow:  https://www.biggerpockets.com/... 

I want to do house hacking and I’m more than fine with being uncomfortable.

I'm sorry to hear this.Contact a local attorney who handles L/T routinely for advice and do what they say.You can likely file an Unlawful Detainer to have her removed.But you might also try contacting her Housing Authority caseworker, posting a notice & attempting to meet with her in person and being extremely empathetic about what she's going through. 

They are also uncomfortable with "confrontation" so they don't want to say no.

Ill definitely be implementing your contacts challenge in my day to day routine. 

My first few inspections were helpful to help understand building systems and routine maintenance schedules (don’t have to worry about that stuff when you’re a renter.)Sadly inspections afterward, for investment properties, only turn up obvious items that’s hard to miss if you personally walk the property looking in the nooks and crannies.Rot, poor wiring, improper framing, water leaks, etc that are behind the walls is when I’ve gotten into trouble.