If anyone has any tips, insights, or just words of encouragement it will be greatly appreciated! 

Train and encourage your tenant to report maintenance, but make it clear they will be charged if they are found responsible.

If you are looking for immediate cashflow, I'd encourage you to explore short term rental or mid term rental investing.

Aside from the horrible context you put the good news in; I do commend you on a successful forray into real estate investing and encourage you to do it again.

Your county property appraiser can help you estimate what those might be, as well as when the taxes would reset.I would also encourage you to look at other recent sales in the area, and compare what others have been paying for similar properties to what you were paying for yours.

However, I do encourage you to think about whether this is something you really want to get into. 

Obviously we don’t want to have large crowds and parties and I’m thinking having that many beds may encourage that.

*Chiming in on insurance - I have a few great brokers I can refer, my personal properties have gone down around 40% YoY.  2022/23 was terrible but there is new (insurance friendly) legislation that has encouraged more companies to come in.

Gold Beach, Oregon specifically encourages tinies in their zoning code. 

What is a good way to encourage them to make the updates so that I stop getting their mail?