Get a small tail to ensure that it stays in your burble
Avoid getting too small of a plug
Avoid using too much lube
If you do decide to get a longer tail make sure to have a plug that is large enough to support it.
Ask your local dropzone about their rules for naked jumping
Make sure that everyone is okay with the Tail Jump including the Pilot (they're the one that has to sit next to you)
Schedule your jump in advanced
Have a plan of action to avoid tandems and other customers