So, even when the market is challenging, you can still see properties and stay current.Don't take a break when the rates are high.

If the tenant stays, they will be on a month-to-month lease, which requires a 30-day notice.

I can't see what you would need a course to teach you that you can't learn by reading 30 Day Stay; listening to the BP podcast episodes with Sarah Weaver, Zeona McIntyre, and Jesse Vasquez; and hanging out in MTR forums/Facebook groups.

3) GPs tout years of experience in this space, how can LPs stay on top of GPs staying on top of hired companies? 

I would suggest getting another full-time job for the time being and investing/doing STR on the side until you can fully and comfortably replace the income that you would be receiving from your job.Is your LTR in need of repair?

Additionally, I would like to attempt to do the process Owner/Builder with subcontracting work out as well as doing some of the work I'm comfortable with (I have some experience with bathroom & kitchen remodeling an am not new to the construction industry).

Those failures are  more negligent than a PM allowing a guest who paid with expectation to stay at the house to remain there in the middle of winter when they arrived on a Friday evening as you described.For now you will have to rely upon insurance, I don't believe the PM acted unreasonably given the circumstances.

So if you discount a small amount to get rolling, that is something that can work, but don't want to stay low for long.You will start to get the dregs staying at your place and they can do some real damage to the place.

The thing about condos is the HOA will go up and your mortgage stays the same so you will end up losing by the end of the mortgage. 

If you're comfortable with waiting 3 years, maybe that's not a bad decision since the building has a foundation that isn't going to fall apart, but yeah it's good that you are figuring out what you need to know to be ready when the time comes.