New to analog

I spent the last 6-8 months building a decent (at least to me) system that I enjoy quite a bit. I sold my CD player about a year ago and currently only relying on streaming. I was in the market for a nice CD player but figured why not give this analog thing a shot and see what all the fuss is about. So here we are :)

One thing to keep in mind is that while I might be a total noob when it comes to analog/vinyl, I've been dabbling in audio for almost 15 years and have gone through my fair share of system. So I have a good idea of what I like -- warmth over neutrality, but not overly lush. I like dynamics but not at the expense of timber and tonality. Mostly listen to jazz, vocals, classical, and classic rock. My system includes ...

Sonore opticalRendu streaming via Roon/Qobuz/Tidal
Luxman DA-06 DAC
Luxman 590AXII
Sonus Faber Olympica II

My goal in building an analog rig is to treat it as a journey instead of trying to get to the end game right away. I want to start with buying a turntable and use the phono stage in my Luxman. Just like other things in audio, I suspect there's a tipping point, in terms of dollars, below which you cannot appreciate what analog brings to the table. I know a few folks who bought fairly low end TTs and gave up claiming that vinyl is no better than CDs. I don't know if that really is the case, or they were playing below the tipping point. So the question is where does that point lie? I obviously don't want to start with SOTA turntables but also don't want to cheapen out so much that I'm not able to experience the magic if you will. So now on to some specific questions ...

1. Since I'm starting out, I want to buy used to maximize value and stay within the sweet spot (whatever that happens to be). Good idea? Or too risky given so many moving parts (literally) when it comes to turntables? Is $2500 a decent target for used and 'gentle' introduction? Feel free to suggest cheaper alternatives by all means. At this point, I want to set the bar to a max of $3000.

2. Which manufacturers/models to consider and which to stay away from? I don't want something that's too complex for a newbie. I know that I will be upgrading in the future so something with good resale value would be nice.

3. I've seen some TTs sold without cartridges. Given that I'm totally inexperienced I think I want to get something that includes everything except phono stage. Am I overthinking, or should I be open to buying separately?

4. Finally, feel free to share any obvious do's and don'ts that I should keep in mind.