This forum is super helpful too so I try to regularly review what’s going on and be as helpful as possible. 

Given the property is located in the Poconos and the property is vacant more regularly as an STR there are proactive measures  you should  be taking such as making sure there are heating sources so that the plumbing does not freeze and ensuring there are no blocks in the plumbing lines with routine checks.

But it’s clear you’re a smart investor who knows the long-term benefits real estate can bring.I keep reminding myself why I stick with real estate: you can make money every month in four different ways:Cash Flow – Passive income to live on.Appreciation – Long-term property value growth.Depreciation – Tax benefits that reduce your taxable income.Tenants Paying Down the Mortgage – Even if you’re paid off now, this is one of the biggest wealth-building tools for leveraged properties.It sounds like your main struggle is the stress of active management—and trust me, you’re not alone.

I have been part of a regular meetup for a couple years now and it definitely helps ground you in your local market.

I'm the VP of a roofing company in South Florida and work with a few good PM companies on a regular basis, a lot of bad ones too.There are good and bad PMs in each of those companies. 

By accelerating your depreciation schedules, you reduce your taxable income which in turn increases your operating cash flow.

If you do so - 100% of the cash converted is taxable.

And while yes, no one has the same pricing (combination of factors), I also continue to check on a regular basis our rankings and how we "present" on total costs per stay vs. our competitors.My gut says there is price creep and we might have a ways to go before the market really corrects.

It's pretty common practice to have something like that in a property management agreement, and if it falls under that limit they're going to pay it and not notify the owner except in regular monthly updates because it is below the threshold of what is an ordinary expense in the course of business.

Unfortunately I feel like a new roof is going to be pretty standard on the things I'm looking at so it might just have to get done on a regular basis.