Would encouraging longer stays realistically help reduce this, especially for a medium-sized cabin?

@Adam RossRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

Maybe look at numbers and properties you could do a potential house hack and begin to plot out moves but I don't want you to fall into the analysis paralysis group and never make a move, have people that will encourage and keep you accountable. 

I encourage you to come with an open mind to new concepts.

We had a client that bought in Port huron and then ended up selling their property because they went through 3 PMCs and gave up trying to find a great one:(Some copy and paste advice below:--------------------------------------------------------------------------------------------------------Recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

In tight inventory markets like Boston, I encourage clients to clearly define their purchasing criteria, start looking, and then be patient.Some of the best deals I have seen or experienced personally happened during unusual circumstances.

Affordable Housing Incentives -While SB 9 encourages new development, it also includes provisions to protect existing tenants and preserve affordability.

You could also offer to cover part of their tax liability through negotiation or encourage them to convert the property into their primary residence to use the IRS exclusion for up to $250K/$500K in gains.

I know some investors who are interested in larger multifamily and encourage me to go find the deals, which makes me really eager to try to get after it.  

REIHub, Stessa, QuickBooks, spreadsheets, etc are all valid tools and depends on the client and how their brain works.I wish you luck in getting yourself organized for the coming season, but would encourage you to make the recordkeeping an ongoing habit rather than a once per year stress fest.