Someone once said something along the lines of "Forget the decisive moment, the hardest part of photography is getting the damn film on the reel" (I think it was John Szarkowski), and there is a little bit of truth to that, as you have discovered.
My favored method to get the film on the reel is not rewind the film all the way, but to leave a bit of leader sticking out. Then, with the lights on I start winding part of the film onto my reel (I use the Patterson). This way I know that the film is latching on properly and isn't getting folded. I then turn out the lights and wind the rest of the film on. Fogging the film doesn't matter to me since the amount I use already starts out fogged. And besides, I don't like contact printing more than 35 exposures at once so I normally intentionally waste a few frames of the roll (even though I load film in a dark room).
Chemicals are easy- I would suggest getting some powdered D76 and mix it according to directions. If you shoot a few rolls of film a month, you should be able to use a gallon batch (which saves money over the smaller ones) and use it up. As long as you finish it up in 6 months or so, it won't go bad. DO NOT REUSE DEVELOPER. It's cheap, and should only be used once for consistent results. Don't forget to mix it hot, but use it at room temperature.
Stop bath can be reused a lot- just get an indicator stop and toss it when the color changes.
For fixer, get a decent rapid fixer. You can reuse it a certain number of times before you need to dispose of it. If you are just doing film (and no prints) you can mix a small batch (enough for one tank) and reuse it the number of times the bottle says you can before getting rid of it. You may or may not be able to chuck it down the sink (with a LOT of water mixed in) depending on your local environmental laws, otherwise, you should save it and bring it to a disposal facility.
Then you rinse (follow the directions on the fixer), use your photo-flo, and dry it before cutting it up into sleeves for protection.
As mentioned, modern B&W films are very good, and it is quite difficult to screw up if you know what you are dong. Despite what some books and people say, B&W films can handle a lot of variance in temperature, agitation, development times, and even exposure before you really start to ruin your images. If properly fixed and rinsed, B&W negatives should also be able to last indefinitely. That being said, you will have to experiment quite a bit if you are interested in maximizing the quality of your images.
If you are doing this fairly often, I would actually suggest looking around and seeing if there is a darkroom club or a photo-club with a darkroom. Sharing equipment can save you a lot of start-up equipment, and will get you access to good tanks, reels, accurate thermometers, etc, and will really be nice if you make your own prints (which is something you should try at least once).
Of course, what I would really suggest is to take a course. There's a lot of trial and error to learn in the beginning and there are a few simple mistakes that are easy to avoid if you have an experience person looking over your shoulder (I almost forgot to rinse my first roll of film). Barring that, I'd get a hold of some good reference materials: try the Ansel Adams trio (Print, negative (this one especially) and camera), or any one of the many guides to black and white film. Also, I'd suggest asking questions on APUG as there are a lot more B&W (and even color) film shooters there.