Questions to ask as I shop for a tonearm?

I’ll be upgrading in 6+ mos. I’m asking now because I’m still learning. I want to take plenty of time to understand the relevant technical aspects of something so complicated & what makes one person love brand X & another person dislike it.

I have a George Warren tt & a Sumiko Blackbird cart I’m waiting for to put on the stock Rega 250. I’m also waiting for Christmas to hookup a Jolida JD9 mkII.  My budget will be ~$1500. While brand & model suggestions are appreciated... I want to learn about tonearms. As always, I appreciate the knowledge you all pass on to me.