However, lets change the fact pattern around and let's say the tree limb falls,  tenants repeatedly report the issue and you don't take reasonable or timely action to remedy the situation.

Different property types have drastically different guest expectations, maintenance needs, and booking patterns.

I think we see a pattern here. 

That pattern of activity aligns squarely with the definition of a Ponzi scheme.If you disagree with the characterization, you are free to provide clarification or supporting information.

I don't know about this cap rate projection, at least in CRe-Retail we project out a 10 basis point rise in cap rate for each year the property ages, so the Cap rate may be 5.5% assuming interest rates don't budge, (probably heading higher as US Govt has to deleverage its last 40yr debt run-up, like we did between '45 and '82, and we did again btwn 1899-1920, same 30-40 pattern going back to mid-1800s)I watched all their videos/podcasts/available webinars.

Find a way to buy off market, discounted properties(Major Key)Add your own metrics to the list above....But once you identify your metrics start analyzing deals and pull the trigger on something. 

Background check must exhibit a pattern of responsibility. - Applicant must be a non-smoker. - Applicant must have no pets except for dogs of non-dangerous breeds.

I could use some advice.... what does the process look like once I identify a company I want to take over for managing the property?

That's a pattern. 

Track patterns, not one-offs .Maintenance triageLife-safety and habitability = immediate.Nuisance items batched into one visit to save trip fees; set boundaries for light bulbs, loose handles, squeaky doors .HVAC filters and tune-ups on cadence with photo proof; replace only when failure or at turn unless risk dictates .Turn standardScope template: paint touch-up, flooring repair, caulk, deep clean, locks rekey, curb appeal.Do big upgrades at vacancy, not with tenants in place, unless safety or leakage forces it .PM accountabilityExpectations doc: response times, approval limits, photo receipts, monthly owner update.Calendar check-ins: delinquency on the 6th, vacancy every Friday, turns twice weekly until listed .Biggest time sinks and how to cut themBack-and-forth on minor work orders: batch and set thresholds; teach PM what’s urgent vs optional .Chasing updates: standardize touchpoints and require proof-in-photos for work done .Overpricing vacancies: use ranges, listen to PM’s on-the-ground read, and choose speed over squeezing the last bit on your first units .Quick wins when inquiries slowPhoto order: lead with the best exterior at golden hour, then kitchen, bath, best room.Price bracket tweak: drop to just under a common search filter and add a move-in credit line in the first sentence.First 5 photos tell the whole story: light, clean, and your three sell points up front.Your next movePick one property.