My managment company has made more than a reasonable amount of attempts to get the HOA to have this repaired. 

(I actually laughed when I first learned this.)10% property management fee (With separate charges for new leases, repair management, and rent collection—what exactly does this cover?)

The city doesn't do much in the winter for residents, let alone the tourists (besides the basics like snow removal).

if you have proper team you can self manage. are you local to the area?

Rentrange uses data from large property management companies just like mine.

For example, one $27/hr FT property manager of mine can manage 140 leases.

Managing remotely works until it doesn't.

When evaluating a property management company, it's important to look beyond just the management fee and consider the full scope of services and costs involved.For example, at our company, we charge a 10% monthly management fee, a $250 lease renewal fee (unless it’s a takeover tenant, which requires additional effort to establish a strong relationship - because usually people are changing pm companies for a reason), and the first month’s rent as a leasing fee.

Buildium is just PM software and has nothing to do with filling or managing vacancies.In regards to proactively managing vacancies moving forward - Buildium breaksdown the number of units 30/60/90 days out from lease term ending.

Not surprised he is a property manager.