However, beyond giving this group an opportunity to do the right thing (I responded with appreciation for the transparency, the only 2 questions we're allowed to legally ask, and a gentle reminder that we are a dog-friendly property and it's a minimal cost of $20 per night), is there a better way to handle this?

Dot dot dot then next question  Happy hunting Thank you for the reminder.

to help track leads, notes  re conversations with sellers, generate reminders every NNN (30 days) that you need to re connect a batch of leads.   

When we have a turnover coming up, we proactively reach out to the landlord to remind them of our process and answer any questions.

You can connect with @Hussain Harun if you would like to be added to an email list that will remind you of the date, time and location of the meetups.

@SharonYour comment reminded me of the family who sold me the deceased home because of his "Porn" room.

I'd remind him that 4 sheet of TP is the norm as he may be using more or there could be a minor blockage that the plumber missed the first time.

Thanks to my W2 career I am comfortable with being house rich, cash poor for now atleast so we will see how this all shakes out 10, 20 years from now.One thing that is true is that property management fees on STRs are an absolute profit killer, and honestly it hurts my soul, but I have to remind myself of the opportunity cost of time saved by doing this, which in-turn allows me to focus on other income generating projects.

If it is a section 8 rental, they would have done an inspection and the tenant needs to be reminded that you (or contractors) need access to repair things. 

It reminds me of when I was first learning to program - any answers I found only led to more questions.