You can get online support for the disk versions, but their "live" support is help from a CPA or Enrolled Agent and only available for their online versions. The support for disk version is mostly searching online to see if someone else has reported the same problem, or asking a question and waiting for someone to respond. I've always gotten answers, eventually, the few times I've had weird questions.
I've used Deluxe for years, and had a lot of ESPP and general stock sales, so I don't see a problem with tax loss harvesting (although I've never done that). There's not a lot of handholding, though, which the Premier might offer.
In my 2018 TTax (disk version), I searched for 1098E, and it came up as part of the walk through, so that seems okay.
If all else fails, you can upgrade your version from within TTax for $30 for Premier, or $40 for Home and Business.