Quote from @Scott Morris: It appears as if he runs one of those programs where they hook you on a low/free cost training and then hit you non-stop with "upgrades", and "higher levels of coaching". 

I currently have QuickBooks, but I'm not sure if it is possible to incorporate maintenance requests/ticketing, late payment notices, and other landlord specific tools.

That's about all I care about as I hold on to the asset that will in 10-20 years be my meal ticket. 

They promoted people who had no training or mentorship to move up2.

It does take some training though, which we provide.

We do annual inspections and monitor the condition and remaining life expectation of big-ticket items like roofs, windows, HVAC etc 

Most of the training is just recycled from others.

The groups that were founded in 2014-2017 have experience relative to those founded in 2021, but the syndicators that have been around since 1992 have EXPERIENCE.I think the three things you outline follow the same train of thought.  

i really want to leave this duplex in a solid position when i move out and rent it. i realize that things WIILL break but i just want to make sure the big ticket items are taken care of.

However, the market has changed in that time period with interest rates changing and homes staying on the market longer and longer.You mentioned the big ticket mechanical items for the house, but it sounds like paint, flooring, kitchen and bathrooms we're mostly untouched.