It's going to be better for you and the snake to start with the tail, and support from that end. Some snakes are cage protective and hiss/strike inside their enclosures but are fine once their out. Not really a big deal, just be careful taking them out.
About the hissing, there are really just two points I'd like to make. First is to keep handling him. If the snake learns that you'll put it back when it hisses/strikes it will keep doing so when it doesn't want to be bothered. That makes it harder if you actually need to remove him from the enclosure for poo cleanings or anything else. The other is that snakes, like most other animals, can tell if you are afraid. If you need to put on gloves and arm protection to make you feel comfortable then do it. You don't want the snake to react to you because you are scared.