How have you handled it when you've purchased a popular existing STR?  

I believe the land where many of these brick and mortar locations exist may ultimately be the prize because they are often well situated. 

Raising rents on existing tenants while maintaining good relationships with them and fixing deferred maintenance items.

Even better, I would like to make it into a heat map with blue pins being lower numbers and red pins being higher numbers.My questions to you all: Does anything like this exist?

After digging into the details, I discovered that no legitimate HOA meetings or member minutes existed.

You could raise your deductibles on your existing insurance policies (consistent with any mortgage on the property) or talk with independent insurance brokers to see whether you can find a better policy. 

I feel like that's a win win for both the landlord and tenant.

Similar situation where I was forced to update while it was occupied.However I know once I have to update the entire unit, I’ll be spending quite a bit as the kitchen is outdated and the place needs paint and either new LVP put down or sand and stain the existing hardwood. 

incentives no matter what aren't going to make the cash flow any better. new builds sell for 10-15% premium over existing inventory on the single family side. 

I allocate most mornings for research and existing clients, so afternoons are when I'm flexible.