We were able to refinance with our go to bank at a decent rate in this environment which allowed us to pull out our initial investment and renovation cost.

Each class you need to take is based on the required knowledge for the next class(s). 

Downside is you likely need to be asset class and location agnostic.

My metro STR is much cheaper(180-280 nightly) and in the “burbs” which tends to be working class clientele, which is okay.

Not having the latter I find myself on a journey to build a portfolio not just for wealth's sake, but to move the proverbial needle on beautiful design and provide a more pleasant built environment for all!

Depends on the Class of the property/tenant.Class A, you may just have occassional maintenance issues.Class B, more maintenance issues, some tenant payment issues, some tenant drama.Class C, a lot of maintenance issues, a lot of tenant payment issues, a lot of tenant drama.Class D, too much to list.

He even teaches classes. 

Happy to talk further on the area (we are large enough to offer options to focus on student rentals/UW Madison campus, and anything from Class C to A locations or suburban/surrounding communities) but to help you consider broad initial search, you could start by deciding how important cash flow is. 

It does cost money and you are required to take classes.

One mistake or big unexpected expense could ruin you if you only have one or two rentals that are not cash flowing.That said, especially in the current environment, if you are coming from a very strong financial position then there may be times where it may fit your goals to invest in a highly appreciating area with no or negative cash flow.