If you are good with fine manipulation and precision type work, something like sewing, you may find it enjoyable. If you find it frustrating to thread a needle and you're rather ham-fisted you may want to steer clear.
I have always had patience and fine motor skills. Every guitar I own has my pickups in it.
You may not be satisfied with the first few but you will get the hang of it fairly quickly.
Advice: The machine guided winding machines will wind them tighter than you can. I would suggest winding your first ones as tight as you can without breaking the wire. You have to develop a feel for how tight that is.
Care will have to be taken to keep the bobbin from deforming. The ends of the bobbin will want to curve up from the pressure of the winding.
Stop winding about every thousand turns to make sure the wind is going on as evenly as you want.
All of your hand guided pickups will be scatter wound. You cannot stack the wire in neat little rows the way a machine can. You will experiment with light to heavy scatter to try to voice the pickups but you will find a lot of hand guided pickups will sound good.
I suggest you wax pot the pickups. You can experiment with how long to leave them in the wax or you can vacuum pot them.
50 years ago I was a boy with no money so I made my first bass guitar from scratch. The only parts I bought were the tuners.
I made the pickup on a winding machine made using my Meccano set.
It worked! Not well, but it worked, and as you can imagine, finding info in the dim and distant past was difficult.
Just go any buy your pickups from a known maker.
You could plant a maple tree, wait for it to grow and then cut it down when the trunk is thick enough for you to make the neck!
Passive pickup winding isn't at all difficult once you understand the basics. That's the knowledge part. Then there's the tooling part which is essentially buying or making a coil winding machine that has a good RPM counter. Finally, buying the components, which may or may not involve the separate act of vintage bobbin building.
I've mentored more than a few folks in pickup winding, both locally and long distance. A decade ago one of my granddaughters, at 12 years of age, was winding good Strat and Tele pickups with my tools and components ... it ain't rocket science. Lotta folks have done it on the low down cheap, which is the hard way to go for most. So, having some disposable cash to get beyond an electric drill winder and pre-built bobbins will make for an easier/faster learning curve. Plus, there are a few tricks of the trade I'd be happy to share with anyone interested.
You say you are thinking about doing it for fun? - I think that's a good enough reason
I started winding my own because I'm just naturally curious
I like it because it's one more thing I can do myself on my guitar builds
I'm one of the fortunate folks that @Rob DiStefano has helped to get started in the right direction - he's a good and helpful guy who winds some excellent pickups - you can't buy that kind of good advice!
There are many 'sewing machine' pickup winder builds out there ... don't destroy a vintage sewing machine to extract a motor and controller. Instead, search Amazon for replacement sewing machines and controllers, they were $15-$20 before 2019, so will be up some but should still be relatively inexpensive.
This video shows how simple 'winding a bobbin' can be, and where people got the idea to tear apart sewing machines (Lollar used to have a book on how he did it). These machines were built in the 1950s the same as the famous guitars. So just buy the replacement motor and controller.
One way to start is buy an inexpensive set of pickups off Amazon/Ebay and replace the magnets and wire but you'll have all the other parts. $15/set humbuckers (are actually quite good, some measure like they are hand wound) where you'll spend more than that for a set of winding kit parts from the usual places.
I gave up the pursuit of winding when I figured out how adjusting pickup heights, tip, screw poles plus measuring actual values of pots and caps and selecting those can push the tone around. If you have a muddy machine-wound pickup you can wire in a series capacitor and it removes the internal capacitance just like a hand scatter-wound pickup.
You can see the simple winding gear Fender used in it's original factory in this video. No counters, just wind the bobbin.