You staying at the property will put you in a much better position to handle guest questions and also help to familiarize yourself with the area as well.  

I am curious if anyone has experienced this and any insight on how to handle.

I'd make sure you have a full service manager in that town who can handle everything for you otherwise that sounds very difficult, especially with the brutal lake winters.

When I replaced an HVAC last year, I listed it as an expense on the spreadsheet I give my CPA and let them handle it.

Are you turning over to a full-service management company that handles listings/tenant calls/maintenance/cleaning/etc.

How do you all handle this situation?

Apps such as AirDNA, Your Porter, Google Suite, Zapier, when utilized together can effectively handle the 75% leaving you to simply take up 25%. 

Briefly mentioned above, property involves legal, financial and civil issues that need to be handled in a timely and professional manner.

You need to plan to deal with these issues before, they even come up & Develop a plan to handle them.Working with General partner or syndication group like ours, can significantly reduce problems, you face as we handle all aspects of property management and you will gain valuable experience on property & investment management along the way. 10 Multiple streams of incomeYour income from your job is only one stream of income, what you want to have are multiple streams of income.Such as Your Income Your Business RE property 1 RE Property 2 Re property 3In Toronto Canada average property is over a $ 1million and it is growing annually at over 10%, which means it is growing at $ 100K annually whereas the average employment income is around $ 40K only.Consider each real estate property as one stream of income, with multiple streams of income, you can be saving a lot more money than what you are earning from your job or business.

The servicer of your loan will handle charging taxes on a monthly basis and holding them in an escrow account and then paying the tax bill when due.