Please share your experiences on some things that worked for you and what didn't work, and also tell me if I am crazy for even entertaining any of this.

Not a good experience at all.If you want others to compare, check out Baseline and The Mortgage Automator.

Competitive Strategy and Operations: How do you maintain operational competitiveness against larger chains like Wawa, especially in terms of pricing, service speed, and customer experience?

In my experience most states have similar laws, though the specific requirements may be somewhat different. 

In Detroit Area, I consider East English Village, Bagley, Detroit University, to buy first house turn key around 150-200k, than after I gain some experience(~6 month) with just renting, go to the next level of complexity and do BRRRR there with people who I can trust after first deal. 

Plus you'll gain invaluable experience being on the front lines.

You have the experience and know how to get the deal done right.

Oh and find a bunch of people who are willing to write you $50,000+ checks despite having no track record or experience.

The Airbnb is an experiment for me, it's my first and will see if that strategy is a good long-term fit for my portfolio.

Getting started is the hardest part of anything, but it sounds like you already have experience renting, holding, and managing property.That's one part of the BRRRR process that is no longer a mystery for you and I think that is awesome.If there are prospective deals that you are considering and would like some assistance for reviewing the numbers, that is one of my favorite parts of being a lending partner.