I feel like I have my bases covered, but am wondering if I'm missing anything obvious or if you have any tried and true questions that help weed out the bad ones.Overall - can you help me get over the fear I'm having about handing my units to a company who (seemingly) will sweep in, re-lease to their paperwork (thus charging me 8 re-leasing fees), disrupt the tenant and their current habits (all of which are well-trained save for an older Section8 gentleman) and ask them to make changes? 

proper notice to enter is usually defined by the state as 24 hours notice. some states require 48. that is your starting point. that being said, coming through with a high amount of showings can be considered as disrupting the tenants right to peaceful enjoyment of their home. if you plan on coming through with one or two, you should be ok (legally) to give tenant prior written notice and come in regardless of their objections. if you think it may take multiple showings, you are likely better off to work with the tenant to set up a block of time for an open house. in extreme situations, you can consider offering a gift card to a local restaurant or movie theater to get them out. the tricky part is striking a balance between what is legal, entering with proper notice, and what is fair and reasonable, since the tenant can purposely leave the house an extreme mess to make it harder to re-rent, badmouth you to potential renters, and may even try to refuse entry. how you approach will depend on your relationship with tenant.

Reliant is a company that has full real estate cycle experience and puts out several deals in self storage a year. 10 First Federal is another company that is younger, only half the age, but has disruptive technology where they replace the on-site operator with technology, which expands operating hours, removes the largest expense and increases NOI.

Some residents will push back on this expansion and potentially move as their suburban-feel is disrupted. 

Will this disrupt my my chances of getting a conventional loan for the duplex?

I also informed her that I didn’t want any disruption to the rental payments as well.  

They've already disrupted my work day FOUR times. 

The sounds from the trains are not disruptive, at least where our property is located. 

what steps in the loan process are disrupted from an unusual sale price number?   

I'm a big fan of Ray Kurzweil myself, and I think air taxis would be disruptive enough that we can't really see around that corner; certainly not well enough to invest that amount of money in one of thousands of possible outcomes.