One hand for you, one for the boat.
There is a lot of good advice out there but, I recommend you read as much as you can. I almost alwas siglehand and I'm still tweaking things. I don't believe a roller-furler is that essential. I don't have one, and it really doesn't bother me. I rig the boat before I set out, while still tied to the dock. I do this for two reasons. The first, I do not rely on my engine. It's a little old, and if your single handing and your motor quits, you want to be able to menuever. Second, when I'm ready to sail, Im ready. All lines really do need to be led aft though. I also would put a downhaul on the jib if you need to. I just ordered, a asymetrical gennaker, with a douser called the flasher/stasher combo. I will probable fly this thing singlehanded, but only if the weather permits. Its a pole-less spinnaker. So this should be intresting. Will let all know how it goes, and if it can be done. You need to be very aware of your skill set also. I have been ion trouble a couple of times, only because I didn't drop a sail before, when I had the chance. (ie before downhaul.) But the reality is check weather, a few times during your sail, (ie VHF, look at cloud formations). If it looks like it getting bad, IT IS. Make preparations early. Other than that, I love single-handing, even when my girlfriend comes with me, I still wind up singlehanding. After a year and a half, she still calls the mast "The big stick coming out of the boat". Cheers TJFlash H26.5PS make sure your VHF works good.