Why do you want an HKS headgasket "because you can reuse it"?
You plan on blowing it?
A metal head gasket is always a good idea, but plan on having both the head and the block surfaces decked to a smoother finish, or you may be reducing the reliability of the gasket.
So, you plan to upgrade to bigger injectors(~$300-$500), but want to know if you can use the stock 22+ yr old fuel pump, instead of buying a $100 Walbro? I'm not seeing the logic here.
Also, if you plan on attacking this 350hp goal in steps(as I recommend), I would do the LSD later. I started with a W58 and an NA diff, and loved it with 250+hp/tq. Keeping the w58 and moving to an LSD(unless you find a 4.1 lsd) will throw off your speedo.
A 3.5 catback is a great start, but won't deliver full potential till you get a 3.5 downpipe. Are you using this catback on your NA? If so, you're probably losing power through loss of exhaust velocity.
As to the other question- do you need a wideband? No- as long as you do all your tuning at dyno sessions. Without the wideband, you won't know where your air/fuel ratio is, and that can be dangerous.