To make the wierd stuff that doesn't justify building a big, involved jig, remember carpet tape. I had to make a 6' long tapered post to repair a bed. I simply laid out the pitch in pencil on a long piece of hardboard rip, put down 4 small pieces of carpet tape, and put the wood on the pencil lines. Worked perfectly. If I were to make it octagonal, I would leave the post long, tack a full size offcut to the tapered end, and run it on the router table (with slide board, if necessary) and a large chamfer bit. You could also do this on the table saw and hardboard/carpet tape with the blade set at 45, but I hate to reset my saw from perfect plumb. Afterward, cut out the part that is the right size.