Yesterday I rode with my two brothers. We rode the routes around the Denton area south of Houghton Lake. Apparently, they haven't had rain up there because the trails were very dusty. Plooms of dust would engulf the entire trail making it difficult to see or breath. Kevin could ride his quad close behind us and keep his head above the roost and dust from the Honda's.
I took my Pilot #2 up there to ride which broke down 20 miles out forcing my brothers to form a rescue team to come and get me. It still was a fun day. The breakdown is at the end of the video. Now both of my Pilots are broke.

https://youtu.be/K4t_t7rJAng

That sounded like a fuel issue to me.
Out of gas, pump dead, fuel filter, pickup lines, float valve plugged up with something.

It's all part of the dance my friend. The more u get to know u r machine you will be able to identify and repair many issues on the trail.
Obiously u enjoy a good adventure and are not scared of going way out ,20 miles,impressive.
I can't say what trail repair items are must haves for the pilot but just off the top of my head I'd carry some easy spare parts with me and a few basic tools.
Replacement belt
Spark plug
Fuel filter
Fuel pump
A short section of fuel line
A couple hose clamps
A short section of electrical wire
Wire ties
And self fusing silacone tape (this stuff is the new duck tape can get it at Walmart for 1/2 the price of discount auto)
Tool wise I carry 10mm to 14mm wrenches.
Screwdriver with changeable tips
Small vice grips
Leatherman multi tool
Last but not least a clean rag.
I carry pre moistened hand wipes. Great for cleaning off after a repair or just wiping the dust off you're face. Also make great toilet paper. Guess they should have been at the top of the list though.

Items and tools suitable for the pilot will vary from mine but will give u some food for thought.
My starter went out one day way out in the woods. Used my extra electrical wire as a pull starter. Wrapped it around my crank pulley and yanked it. Started right up.
Point being u never know what u will need but if you have a few basic items it might just save you're day.

Another thing I do is any tool I use on the buggy goes in my tool box on the trailer with all my spare parts. This way I always have any tools I may need no mtater how far from home. . I also have a vise welded to my trailer as well as a small generator and air compressor. I tend to go over board some times but I'm an old school Boy Scout,be prepared .

daddyrat where are you from? I'm in Lansing and have been looking for good trails to take my 350's out to. Have you been to the mounds?

Pilot #1 troublesome Ohio......................................Plugged exhaust, intake and vacuum feed. Leak down test failed. Better than it was, but drops pressure in seconds. Will look further if my tool or installation of tool was the cause of the leaking. At this point I am saying that is my problem.

Pilot #2 Florida.....................................................compression previously tested at #162 psi now at #24 psi. Bummer.

Ohio pilot: Probably that main crank seal.
Florida pilot: Possible girl machine. Needs better fuel than a boy machine.