I do one wheel at a time. I do not support anything with a jack stand. It is simply an extra backup in case the jack fails. I have never rotated tires on a trailer, but if I did it would be more involved getting multiple wheels off the ground at the same time.
The challenge is you can only place the bottle jack and saddle OR a jack stand directly under the leaf spring area at a time, not both. Raising or supporting the axle at any other point further inboard would be risky IMHO.
I use my floor jack to simultaneously raise a second tire if that becomes necessary. I have a JEG’s aluminum 3-ton floor jack that works well as it can easily “cradle” both u-bolts from under the spring pack for a safe lift. I still place a jack stand slightly inboard just in case the floor jack fails.
I don’t know how to safely get a jack stand directly under the spring pack unless you somehow jack from the frame rail. This has its own challenges.