It's still worth noting as well that just because you're friends with someone doesn't mean you should skip out on any contracts or paperwork either to keep everyone happy and protected 

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?

A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings.

Each guest pays $29-49 depending on property size and that provides up to $1,000-2000 in damage protection in lieu of security deposit to satisfy the owner and avoid deposits. 

I'm operating from a distance and in person meetings with prospective tenants won't be possible.I'm not sure that "age of social media profile" would indirectly fall under a protected class (such as age)?

A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings.

Aside from well drafted contracts protecting all parties to a business transaction, the process of preparing and executing contracts in itself slows down processes and allows for more thoughtful decision making, diligence & vetting.

I've exercised so much grace and patience with this guy throughout this year 1/2 debacle, so him threatening me while I'm trying to make sure I'm protected really doesn't feel good.

2) How do you balance upgrades/cap ex to protect investment versus over-investing, because it is not your forever home?

One of the structure that was recommended by a US-CAN CPA to avoid double taxation and stay protected was the following: Real estate A is owned by LLC A, Real estate B is owned by LLC B, Real Estate C is owned by LLC C (or you can put some of them together instead of having many LLCs).