I think that there will be differencing of opinions based on each of our experiences, outside of what is the norm.

You would not do any significant raising of seedlings. I like to leave them at the same level for the first potting up.

The raising would generally be done when you felt the plant had outgrown it pot or every other year. This will be different for all of us, as some have a much longer growing season. i.e. Larger plants.

The height you raise would probably be no more than an Inch or two,
many have raising substantially higher. You never want to bury deeper though.

Not sure that you can put an age on when to raise. The factor that would make it necessary would be out growing it's pot.
I prefer to let my seedlings after their first potting up, stay in those pots for atleast a year. I experimenting with many of mine. Leaving them potted at same soil level, but in a little deeper pot and not so much wider.
With Obesum's and subsequent X's, they grow a bit deeper than the Arabicums which grow wider across the soil ( their root structure and Caudex as they grow older ).

Many have cut the tap root and replanted. Some cut the tap root and place over a small disc of plastic in hope to have the roots grow outwards instead of deep.
There are a lot of interesting manipulations happening with them.

Rick

Hello again Tori, once again, sound advice from Rick :)
I repot/refresh my plants each spring, not necessarily into larger pots each time though (unless they need it) but into fresh mixes. I have 5 larger ones and several youngsters (not exactly seedlings, but 3-4 inches as my growth rates are rather slow here in the UK). I don't lift the larger ones now, as I think they would become too unstable. The younger ones I will lift no more than 1/2inch or so due to their size. In my opinion, the majority of the caudex growth happens underground, they will put on some girth above soil level, but it's not as noticeable I find.
Thin wispy roots can be trimmed flush with the caudex if you like the 'clean shaven look' and there are plenty of feeder roots left. Wrongly placed roots, even thick ones can be cut off sometimes after they have hardened/calloused over. Slightly thicker roots can even be twisted or moved around to create interest when you re-pot/lift.

Gill UK

Thank you both so much really appreciate the advice!