I really like generator lights. If you don't want to go with a generator hub, I'd recommend the Bausch und Müller Dymotec 6 sidewall generator. It runs about $50, and worth it: the roller is replaceable, and tension can be adjusted from very light to quite heavy enough to give traction in the rain or snow. I've used one for some years now, and won't be buying any other sidewall generators in the future--I've used about four other models. For the actual lights, I like the Lumotec Fly IQ plus, a quite bright LED with standlight for around $75. For a tail light, I'm not too choosy. Anything with a standlight is good enough, and it's easy enough to run two taillights, if you like. On my main commute bicycle, I have a fender mounted light from AXA and another on my rack (also AXA, I believe), both powered without any problems from the dymotec. So for well under $200, you can get together a quite good generator system. I have a B & M CYO IQ Plus (around $100) on one bicycle, and it's quite bright. With your budget, you could get the super duper $160 Luxos B (but not the $230 Luxos U), two taillights, the dymotec, and still be within your $300 budget.