Personally, I perceive a fair amount of risk in the market.  

A few things to keep in mind: the entire operation must be outsourced, and neither you nor your immediate family members can't be involved as you are considered "disqualified persons."

Nowadays I use what I've learned and help investors building their rental portfolios in class C neighborhood while personally I either build Padsplit in class C or build high end vacation rental in class A area and hold them. 

The reward must be greater than the risk.

I also know that in many cases the llc will protect my personal assets and I fully believe this is either analysis paralysis or just fear of failure.Thoughts on how to get past this and where you recommend starting?

As well as guest room in the main house.These properties are all personally owned and obviously highly leveraged.

Regardless, it speaks to him being a high maintenance person I don't want to rent to.

I haven't personally gone myself, but plan to soon.

I'm personal friends with the owner and they do a great job. https://www.livindy.co/ 

I was wondering if I should set up another personal bank account for all activities.