As a single pilot captain flying the Ultra, Primus 1000, stocked...3 EFIS, 2 MFDS, 2 FMS...for me the issue wouldn't be the gear, but the speeds and having to deal with a crew member.
I'd be tempted to fly it single pilot and maybe trade seats with the copilot for his PIC empty legs to get some experience.
That might seem blasphemous for the crew concept folks, but just about every aviation accident we have are two guys watching the ground come up...maybe just having a right seater 'watch' and step in if he needs, rather then find things for him to busy himself with might be a better way to go for a transitioning single pilot captain.
Keep in mind they tried to certify the Excel single pilot.