PADS Pro is difficult to learn, and the documentation is pretty bad. One trick, if you have a maintenance contract, is to put in a support request for something you're stuck on. Most of the time an support engineer will contact you within a day and you can generally get them on a webex to help figure out what's going on and this is a good opportunity to ask any other questions you have. I haven't used Altium or Cadence products for several years, but I don't remember it being easy or even possible to do a webex with a support engineer.
They also have some decent on-demand training - you run through some lab exercises on a pre-configured AWS instance. I'm not sure if this is available for evaluation versions of the product, but I think it's included if you have a license for PADS Pro.
The version of Hyperlynx included with PADS Pro won't simulate vias at all. I think the lower-end 'stand-alone' versions have analytical via models good up to several gigahertz and above that they recommend using their full-wave solver to generate s-parameter models of the vias. Like someone said this is pretty well automated within the tool. The DDR wizard is a pain to set up, but it seems very comprehensive and can catch some really subtle layout mistakes. I've never looked into pricing on Hyperlynx, but I suspect it gets pretty expensive. The rental option sounds like a good way to go, or maybe finding someone with a license and hiring them to run your sims.
Intel/Altera has published some really good app notes that tell you most of what you need to know for high-speed routing... see AN-672. They did a bunch of sims on various anti-pads sizes, via clearances, etc., and just following their guidelines may be enough to get you a working board, even at 28G.