Cricket (scoring variety) is my favorite game as well, macro.
Whatever you choose, I think you'll have fun for sure. My earliest league experiences were in soft tip and we certainly did have fun, but then there was something that was more alluring to me about the original steel tip game. If you already have a bristle board I'd think that steel tips would work best. However if you start to like it a lot, you could get an electronic board too!
The convertible sets (replaceable tips where you can switch out between steel tips and soft tips) may be a neat way to go. I cannot recall the brand now, but I have one of those too for that transition time when I was playing alot of both styles. There are also hammerhead style darts with tips that slightly give when they make contact that help to reduce bounce-outs from hitting wires, etc... I am sure there's lotsa new stuff now from the last time I looked seriously that macro I am sure is more knowledgeable about.
Shaft length I think will be based on your particular throwing motion. I'd start with the mediums personally and see where you go from there. Or get a couple sets and see which on works since they are not that expensive.
I have a fairly nice backer board with slide out "drawers" on each side that contain dart storage and chalkboards. It really depends on how nice you want it to look, etc. I'd use some kind of backerboard even if you go with soft tips.
Also get some flight protectors. Those are inexpensive tiny little metal slotted "caps" that fit over the ends of the flights keeping them spread out better and reduces the chance somewhat of an incoming dart splitting them.
My buddy and I try to play whenever we get together. However that is rare nowadays but this discussion (if you cannot tell
) is rekindling my interest! I was never as good as he was, but had my highlights (which I am now fondly recalling thanks to this thread!) and certainly my share of enjoyment from the sport.