Here's another vote to move on up to Legacy, with plenty of run-on sentences for your extended reading pleasure.
I'm just now into O gauge (about 4 years now which makes me a huge newbie) and I made the investment early on, after wanting more than just conventional running and extensive reading here on OGR and other places. I pre-planned for it all on my new-ish layout.
I have the Cab2 controller and base, running three loops with a ZW-L in Command mode (runs conventional trains just fine that way too by varying voltage from the Cab2 with the added coolness of built-in voltmeters) and 11 FT switches all in CC mode as well. Was able to pull all the switch wiring off the actual switches and use power from the track, using the Cab2 to run everything, and it made the layout wiring Much Simpler. I've got the Sensor tracks on all three loops, and the WiFi setup as well. With the sensor track, I have found I was able to set a previously unprogrammed Legacy engine on the layout, gave it an engine number, ran it around a loop, and the sensor track picked up all the Legacy details from the engine as it passed over, and automagically put all the Legacy details into the Cab2, not even having to load the orange plug for it. Don't know if they all do that, but mine have, and it's the coolest thing ever. And the Cruise Control on the newer engines, to me, it's an Absolutely Must Have. One of my loops has 4% grades (layout is only 8x12), and while my TMCC engines struggled up and over, with the Legacy you set it and forget it, and up and over she goes with nary a wheel turn. Awesome stuff. Runs my TMCC engines very smoothly too, but I almost never run those anymore. Since I love to run them all at low speeds, it works out great.
I've used the TMCC Cab1 several times with the local club layout. also helping others with the DCS setup for their engines at the the club, and hands down the Cab2 is miles down the road more advanced, and more importantly to me at least, simpler to use. Easy to set up and program. Easy visual confirmation of what you're doing and doing it with. DCS has too many finicky bits for my taste with the signal weirdness and wiring needs. Again, this is MY opinion only.
it also has changed my buying habits. I am ONLY interested in Legacy engines now. I've saved all sorts of money (in a twisted sort of way) by only seeking out Legacy and Vision Line engines. I have a couple of LionChief and LionChief Plus engines, and they run right alongside the Legacy, when I run them. They just don't have the Cruise Control or the awesome sounds of Legacy, so are sitting on the shelf more and more.
My 2.5 cents with a bit of extra change thrown in...
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