The transfer process is really simple as long as your recipient has or is willing to take two minutes to set up an online Gopher Sports account. You go into your account (either online at Gophersports.com or in the Gopher Sports app), identify the tickets to transfer, input the email or phone number of the recipient and the U sends a notice to them by email or text. Recipient gets a notice and has 48 hours to accept the tickets or they get returned to your account.
Can't help you with Holiday.
When this was initially discussed, they had a plan for accommodating those unwilling or unable to electronically access tickets. I think it would involve picking up tickets each game at will call, but I'd check with them to see if this idea has carried over. I know a long time Twins season ticket holder who has similar issues and has been told they will not be issuing physical tickets or accommodating those who cannot use e-tickets, so maybe the attitudes toward this have changed across the sports industry.