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."

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?

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. 

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

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

I am looking to borrow 50k from equity in a 4 unit investment property to use as a downpayment on a personal residence.