Hey I’m sure there are plenty of more qualified people to help you here but I’m always looking to help out a fellow Jersey man!
1. When you stretch you want to be flaccid, if you get hard AFTER the stretching is completed I don’t think there is anything wrong with that. In fact, I would prefer that because then I would continue with wet jelqs. It’s good to have some wood when you are jelqing, it helps fill up the cock.
2. I am circumsized as well. I’m not sure about squeezing all the veins in the penis? There are videos and many descriptions of wet jelqs. To me it is not so much about squeezing the veins as getting a good hold at the base of the shaft and sliding upwards toward the head. Use a standard OK grip or a reverse OK grip. Also do not forget when one hand gets to the head that the same motion is repeated with the other hand, and continue, very similar to milking.
3. I would continue doing the newbie routine until your gains begin to slow. I am currently in the newbie routine. Most people say stay with it for at least a couple months, you need to condition your cock for more advanced techniques down the road. You also want to grab any quick and easy gains you can get from the newbie routine, and once those gains are exhausted you can step up to more advanced exercises.
I’m also more or less a newbie so someone else might want to chime in but this seems to be what I’ve learned thus far. Keep on jelqin and representin Jersey yo!