I'm a broker, investor, and PM here in Sacramento -- we manage over 100 investment properties, mostly STR and MTR. 

What kinds of software have you used to manage your properties that you would recommend?

BP is a fantastic resource for learning about real estate investing, rental property management, financing options, market analysis, and much more.

If you run the income and expenses of the property through the LLC as a management company that may help your credit down the road.

I understand you can find information about analyzing deals for STRs and managing STRs on YouTube etc, but wondering if anyone has found a coaching program worth it?

Perhaps you keep a few that are easy to manage to pass onto your heirs so they can get a step up in basis. 

I've managed over 1000 residential units in my career (so far) and I've seen this plenty of times.

I don't want to deal with property managers, let alone tenants who will get on my nerves by failing to pay rent or demanding a new stove, refrigerator, window, HVAC and etc., and breaking the drywall and kitchen cabinets with sledgehammer if I evict them for non-payment of the rent.

Our efficient project management ensured timely, on-budget completion.

Also, make sure there is some kind of waste management agreement.