Usually replacing the bushing and the bolt helps tighten the assembly.

As far as the rear shock is concerned: I was mistaken because according to you its measurement is correct.  How's the ride on that shock.

Yes I think this is my strategy now.  Addressing the free play.
And maybe adding a “lift” to the contact patch of the side stand.

In your case, the suspension has not been lifted; the swing arm and wheel assembly seems to have been extended by a shock absorber that is too long.

Concerning the side stand: What's normal in an fully-extended side stand leg is not much play at all, but play increases with usage. The bolt that mounts the side stand fits into a bushing within holes in the side stand yoke. When the bushing wears, there is more play in the side stand leg. When it wears excessively, the bolt that attaches the leg may deform the mounting holes and cause even more slop.

As has been indicated by Edward, material can be added to build up the side stand foot. Some owners have installed lifts under the foot made of aluminum, steel, or other solid material. Verify that whatever is used, it does not contact the muffler. If the rubber stand bumper is in reasonably good condition and not wobbling in its mounting, when excess play is eliminated from the stand leg, it should nest into the bumper when lifted.

13.75" off the Brick?

But I think the suspension may have been lifted via the shock/spring.
when on the center stand, I can move the side stand up and down about 2 inches.  There is definitely give, but not sure what's normal.

In your case, the suspension has not been lifted; the swing arm and wheel assembly seems to have been extended by a shock absorber that is too long.

Concerning the side stand: What's normal in an fully-extended side stand leg is not much play at all, but play increases with usage. The bolt that mounts the side stand fits into a bushing within holes in the side stand yoke. When the bushing wears, there is more play in the side stand leg. When it wears excessively, the bolt that attaches the leg may deform the mounting holes and cause even more slop.

As has been indicated by Edward, material can be added to build up the side stand foot. Some owners have installed lifts under the foot made of aluminum, steel, or other solid material. Verify that whatever is used, it does not contact the muffler. If the rubber stand bumper is in reasonably good condition and not wobbling in its mounting, when excess play is eliminated from the stand leg, it should nest into the bumper when lifted.

The shock is too long and it's not OEM. Remove it from the Brick and measure it from the center of one mounting eye to the center of the other mounting eye. It should measure approximately 350mm or 13.75". A popular basic shock for replacement is the YSS ECOLINE ME302-350T.

Before you do that, there is a silver colored adjuster at the top of the shock. Tell us what happens when you rotate it fully to the left.