Johnny20
For me, I only bring the basic tools like flashlight, whistle, spare belt, vise grips, tow rope, spare plugs, spare hat / gloves and my cell phone. Basic tools to help get me unstuck or to fix most common problems. Or, keep me warm - if my primary hat / gloves get wet. If I load down too much, I'll need to tow along an attached sleigh. LOL! Start with the basics and add more later on - if more tools are needed.
I would agree about joining a club. For me last year, I joined 2 local sledding clubs and am a guest for next club over as well. Thus, I can go sledding every Saturday or Sunday each weekend (when the trails are open). While stopping on ride breaks with others, I also meet new people and collect their name / cell numbers. Meeting new people and networking (and learning about their previous lives) is amazing. And, I learn what works or doesn't work for them. For example, the one older age guy I met stores his sled an an enclosed trailer during summer months but uses his open flat bed 6x10 landscaping trailer to trailer his sled around during winter months - cause its lighter weight and easier to see / backing up. And, they also share what bush trails should be avoided due to difficult riding levels and/or out of cell phone reach. Will probably join 2+ clubs this year (to collect more sled buddy names) then book new buddy rides with others. Especially with the folks who do same "put put" speed as me. LOL! Best safety advise is, try NOT to sled alone. There's times we must sled alone (re: to get to trail head opening to meet one's sled buddy) but in the deep bush trails, always go sledding with a buddy (who drives his own sled)....
Hope this helps...