My plumber in the Triangle doesn't want to travel to Greensboro for smaller fix-its, and I have two smaller repair jobs. 

If you could share your recommendation and any insight on their working habits or expectations it would be very much appreciated!

A legal structure can serve you(and your partners) for the long-term, so knowing where you want to travel plays a big role in deciding what path is right for you. 

The fact that I don't bite as a habit is a clear matter of education. 

All policies are different, but generally it is something like this.Homeowners: Covers structure, personal property, and personal liability and legal expenses.Landlord: Covers structure, lost rent due to non-habitability due to covered event, personal liability and legal expenses, and YOUR personal property like a washer/dryer or furniture if you rent the place furnished.

I have struggled with this my whole life, and am kinda getting sick of this fear I have, so I've been taking steady steps to address it, i.e. developing small habits to push me in the direction of my goals, so I'm not as fearful when it comes time to pull the trigger.

In a nutshell, my educated guess was these tenants are living in barely habitable units because that's probably the extent they can afford. 

I'll try to make these two into a habit, it sound like it'll do wonders in motivation!

I’ve made 6 figures consistently the past few years but I’ve spent most of it on high rent, leisure & travel to be honest so only have about 40k liquid for a conventional downpayment on a 200k property.

Once we achieve financial independence, I would love to travel the world, work as a freelancer if needed and spend time with family and work on my hobbies.