I personally like working with a broker because I know they are helping to vet the insurer and making sure that I am not missing key pieces of coverage.That said, from my understanding of the insurance markets basically different insurers like to spread their risk out across geography and asset class.

It will familiarize you with the basic terminology and benefits.

I will be making $55-$60/h by the time I’m certified at 21/22.I am also looking into side hustles to increase my income such as flipping cars, reselling etc.As of right now I have around 8k saved, and 5k invested in stocks.Obviously I cannot buy a property with just a few grand right now, but basically I just want to ask for any advice or tips you would give to me or your younger self when you started.I usually listen to audio books on personal finance and business while working instead of music to further my knowledge.Any sort of advice is welcome, books, podcasts, methods to learn about.

We basically have been paying out of pocket.

In my experience, NARPM designations provide a solid foundation and are a great starting point, though they are more basic.

In many jurisdictions any lease 24 months and longer basically conveys additional rights and a simple eviction is no longer feasible. 

These are just a few basic things I'd look for.In reference to the agent, you definitely want to find the investor focused agents that does a lot of deals and lean on them for their expertise.

These regulations are basically trying to prevent all unsolicited calls and text messages to people with whom you don't have a prior business relationship or permission to contact.

Basically, they are a turnkey STR company. 

I've had kids tell me their heat is not working and they never turn on the thermostat, etc, etc.