I have a semicircular drive that was installed at about a 7 degree decline from house to street (drainage/lay of the land)

The driveway is stone squares/rectangles.

Currently using chocks and cinder blocks behind the chocks. Also attached a wheel claw to each of trailer wheels.
Also used some cable and chain to anchor the trailer to some trees on the uphill side of the drive (I know this is over doing it, but thought I might as well).

My main concern is that little front wheel on the trailer. I chocked it and surrounded it with cinder blocks.

That front wheel is designed to spin and rotate when not under load, and I know it's unlikely it will move under load on a seven degree decline, but any suggestions to lock or prevent that little front wheel from somehow rotating or rolling?

There is a commercial donut like device made for that.

If it's a solid wheel, drill a small hole in it and run a cable or wire through it. Attach other end to trailer tongue or cinder block.

I think you've got it pretty well covered

You should have been an engineer, because you sure do know how to overthink things.

Genius

Will also look for the commercially available doughnut device.

I was raised by one (chemical engineer).

Everything was graphed out decision trees, flow charts, protocol, and lists.

And to think..... all I do is put a couple small rocks in front of my jack wheel to keep it from rolling......

Throw a couple of bags of sand around it.

I think what you have done would be required....if you lived halfway up Pikes peak....

Thought about that--I like this
Got some 40# bags of milorganite and some 50# bags of pea gravel in the garage.

This is getting out of hand

You could throw a couple of 50 lb bags of sand in front of the little wheel as an added safety measure. Just saying

I bought a $4.99 circle made for the front wheel from academy and a $4.99 wheel chock.

Never did anything for the skeeter