Hacking I just ordered a New 3DSXL - Correct me if I'm wrong:

[Quantumcat]

Okay so transferring will definitely lose illegitimate titles, regardless whether cfw is on the target console. Good to know. Is it possible to link my nnid to the new console without system transfer? As in, unlink from old console, link to new console? Cause if the homebrew stuff doesn't get transferred anyway, I can set it up fresh as well

It will be transferred, you'll just have to install the tickets for it to show up. You can do this by backing up the tickets on the source before the transfer and restoring on the target after the transfer. You can move the NNID by calling Nintendo and saying you lost access to the console it is currently linked to but they may or may not agree.