I've used lots of, well almost everything from butane powered (20 year old models - 15 years ago- todays butane one I have *****) to 12 cigaret lighter models, from (then)$200 soldering stations to simple plug in irons, to the pistol every mechanic buys off the truck and should almost never actually use. I've got several 225W and up antique Stanley and others, and even a Coleman AA powered easy heat.
Weller makes good stuff (personal choice) as does Elenco and Hakko. At work I'm the only one with any real soldering experience (and yes, the head mechanic has that same soldering pistol in his box). I've got a weller sp25 and an SP60 in the shop. Standard hardware store plug in irons. At home I most often use my Weller ht202 soldering station (with a 60 watt pencil point).
you don't need anything fancy, especially if you're going to be working on equipment and in a shop - get a plain iron like the SP60. Chisel tip is fine - conducts heat more efficiently to larger connections. Unless you're soldering big wire (8 or bigger) 60 watts is the best balance between size, capability, and heat. Too much wattage (100-125 watts) melts insulation very fast, and as mentioned those pistol style consume tips.
I would recommend an iron stand in addition to the tin bracket in the SP package. They are cheap and much more secure, plus it can be modified with a magnet under it to stay put on a bench, tool box, or vehicle. something like this
Use rosen core solder, never acid core (which is for plumbing and will eat the iron's tip). You want thinner solder - plumbing solder size will be too thick for most electrical connections. I like .05 myself.
Paste flux is easier to work with and normally the plumbers stuff is ok (I use the red at work and have several tins at home so old I can't read the labels anymore) but stay away from acid flux or liquid as it's normally acid and again, used for plumbing. Acid flux will not only eat the iron tip but attack the connection and wire.
One of those steel wool looking things for tip cleaning is nice but unnecessary - a small piece of sponge damp with water, or even a folded piece of paper towel damp works fine. That's all the old soldering stations used to have - small tray with a sponge.
