Congratulations on your recent birth!
I "worked & pumped" for all 4 of my children, and I'm a childbirth educator so I've been sent samples of several types of pumps, so I'm intimately familiar with the task you are trying to do. But my youngest is 3.5 years, so I'm getting a bit less familiar with newer pumps on the market.
I mostly used a Medela Pump in Style since I was working full time. It is awesome...just to plug that in case you will be going back to work. On manual pumps, I *HATE* the Ameda pump that is given out free at many hospitals in the "breastfeeding diaper bag." It hurt my breast and my hand when I used it, and it was hard to get much milk. I am an "easy pump" so ultimately I would get milk, but I only reccommend it in an emergency.
I do like the Avent Isis and the Gerber Massaging Manual as far as use goes--both are comfortable for the breast and the hand (ergonomic design keeps wrist straight and has a large pumping handle to spread out force over your hand). I've heard that Dr's Browns has a pump out now that is similar to the Gerber, but I've never seen it yet. The Gerber pump is a pain in the neck to take apart to clean, which is its major drawback. The Avent is easier. But the Gerber is a great design for sore nipples as it puts less suction stress on the nipples.
When using a manual pump, you should pump only until milk starts to let down, then hold the suction at a comfortable level while the milk sprays until it stops. Then start pumping again until it sprays again...
Pumping in the morning is usually the easiest as you have the highest milk supply then. Pump after your baby eats, not before to ensure the best supply for the baby. On days I was at home I would generally nurse my baby, then spend some time playing with baby, eating my breakfast, then nurse baby to sleep for a nap, then I'd pump while baby was sleeping. I wouldn't necessarily pump immediatelly after nursing the baby down to sleep, but I'd make sure to get it done while baby is sleeping. If you have to pick between pumping very soon after the end of a feeding, or very close to the beginning of the next, I'd go with the beginning, just because a healthy baby can ALWAYS pull out more milk than the pump, and you are constantly making milk, so you will not short the baby if you pump before, but as you mention, if you pump after and baby has eaten a lot, you might have trouble getting milk.
Pumping in the evening, unless you have an over supply, is likely an exercise in futility. You are already tired from the day anyway, and your milk supply is reduced (this reduced supply is why some babies "cluster feed" in the evening). I would nix evening pumping sessions unless you are separated from your baby at that time--like for a part time job, or because you are out for an extended date with your hubby (but babies at this age are so portable...I always brought mine along when hubby and I went out).
Good luck!
P.S. One other poster said "Milk is watery when it first comes out at each feeding and then gets thicker as you nurse. The same is true in the reverse, if you pump then nurse, the pumped milk is more watery and less fatty which stisfies the baby longer."
I'm sure this poster just accidentally left some words out here. The "watery" pumped milk in this scenario that is low in fat would satisfy the baby *less*. I think what the post meant to say is that since you have pumped out the foremilk, when the baby nurses and gets the hind milk--which is more fatty--the baby will be satisfied longer.