The biggest stumbling block I see is not really knowing the Garmin 430 before you show up in Duluth. (This for Avidyne models, I haven't done any training in the Perspective yet. I'm still learning the thing myself.)
If you have some experience in the aircraft it goes easier, but the CSIP course is basically the same as the new owner transition course, with some additional detail. If you study hard ahead of time, do both workbooks and show up prepared it'll be fun.
The downside is it's expensive and it can take some time to recoup that investment if you don't have access to a ready pool of Cirrus students. The recurrent training market seems to have slowed quite a bit as insurers have relaxed some of their requirements. Also, most Cirrus pilots seem to already have a CSIP they've been working with, so getting recurrent work can be difficult.
Transitions for new owners almost all seem to happen up at the factory.
I do maybe four or five transitions a year for a flight school I do some work for, plus a bunch of other Cirrus flights (instrument currency, second pilot on a trip somewhere in scuzzy wx, that sort of thing) but get almost zero work "off the street" as an independent.
It's a really fun airplane to learn, you earn your money when it comes time to teach it because it's hard work and it takes some effort to stay on top of everything if you're not doing it every day.
And yes, guard the stick on landing as PIOs are common as is getting too slow and starting the flare too high. I tell everybody to drive it down to the runway until you think the nosewheel is going to bury itself, take a breath then start the roundout/flare. If you manage the energy and airspeed precisely it's a really easy airplane to land.
Renewal is $95. If you attend the annual CSIP Symposium in Duluth you're automagically renewed for free, regardless of what training you've done in the past year.
The other upside is learning to teach the glass and systems on the a/c are a good foundation for transitioning into the avionics on a jet. Or at least that's what the jet drivers I've been working with lately have told me.