As for the rest of it, you can find a lot of useful tips on past forum posts along with podcasts and youtube material on the topic (BP and other RE sources).We've self managed STRs for a few years.

@Gutta Bunni are you advertising your management services?

Quote from @Max Pergament: Quote from @Matthew Irish-Jones:Licensed and insured to manage third-party properties. 

I personally do not have experience managing rentals.

We have a property management company and real estate brokerage. 

I'm a Real Estate Broker/Owner and I own 5 doors that I have been self-managing as MTRs for the past 5 years.

One of the most important steps you can take as either a startup landlord or seasoned one is to use a platform specific to property management as it will elevate your operation and save you tons of time.The good news is that nearly every software designed for landlords includes these features.

This also leads owners to ASSUME simpler is better when it comes to management contracts.

I individually priced all my materials and got several estimates from contractors.

@Kyle McVay I self-managed my first 5 units and then transferred all new units to a PM.