Is there a point of contact person/business that handles all home investor concerns (general contractor, engineer, etc.)

You can probably meet him in person if you attend the next HH.

Now we are in 2025 and although I still own the trucking company, it has been an inconsistent pit that has technically brought me personally no profit.

Fewer still actually show-up to deliver the value in-person. 

He personally screened every tenant, handled every maintenance request, and even showed up to mow the lawn at his properties when the landscapers were running late.His phone rang constantly—contractors, tenants, vendors—all needing his immediate attention.

Someone local who has familiarity with this would be your best person to give you the information you requested.

How often do you use it personally or let friends/relatives stay? 

For me personally, I am hesitant to sell unless it really makes sense.

Myself personally I'm invested in Buffalo and NYC, but that's because it made sense for *me*. 

Look into DSCR loans, which use rental income for qualification, allowing you to scale without relying on personal income.