If you’ve got property and aren’t well-versed in an accounting software I’d recommend starting with a good accountant and quickly adding a good bookkeeper.

Some folks have already given good advice, and I want to add a quick tip for how to get data on potential STR properties.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

And what about that high school biology? 

If anyone tells you that you can get 15% cash-on-cash it's either a scam or ultra high risk. 

In '23 the state set records for tourism revenues and visitors to the state, a hat tip to your point about year-round demand. 

@Raiyan KhanYou can search these forums for vendor recommendations but you can also join a real estate investment club in the area you want to invest and get the same info.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

You input and recommendations are greatly appreciated. 

This is very common, and highly successful.