I have loaded a 2017 Honda Pioneer 1000-5 in the garage of a 2020 Momentum 28G.
My Pioneer has the Honda plastic roof on it (which adds 1.5-2"). First try, roof rubbed on under side bracket of Happijac bed, as I pulled in forwards, but couldn't get past it. Removed plastic roof from Pioneer and pulled in, but barely had room.
Had my grown son sit in passenger seat and deflated tires in Pioneer to lower it for clearance and was able to pull in forwards. Left him in passenger seat as I strapped it in.
Then, this weekend, we dropped the lower (sofas) of the Happijac system to side walls and I backed in the Pioneer. I got it in and over to the side with clearance and no passenger in the side by side. I did have tires down to 5 lbs to back it in and put in 4x4 to back up the ramp but it did work.
Also of note, I upgraded from regular ratchet straps to the ShockStrap brand. These hold better so the Pioneer isn't bouncing and trying to knock my cabinets off of the walls, as I drive.
I am still sorting out the best way to load the trailer for towing, to avoid sway and bounce, but getting closer. Blue Ox SwayPro 2000 on an F250 for me.