I'm fairly outgoing, but am beyond awkward when trying to introduce myself to someone. 

It would be awkward for only one tenant to have a bell at the front.

Dumb question for all those rehabbers, contractors, and flippers out on here. I need to replace the garage door on a house I am rehabbing, and it is 6'6 tall. Seems that the standard height on doors these days is 7'. ...

Main priority is that we both mutually benefit and secondly, no awkward family gatherings where we sit at opposite ends and can't even look at one another

This makes things less awkward and will save you time in the process. 

VERY awkward layout for sure. 

Not everyone knows people in this situation and/or may feel awkward asking people for this investment.

Sometimes I feel awkward when I need to ask for late fees from tenants so now I'm using Tellus App, a property management software, which can automatically charge late fee when the tenants miss the payday.

This puts me in the awkward position to have to communicate with the tenant that I'm essentially evicting.

It was awkward and not as easy as most people say it is.