I have a Poulan Woodsman, 36cc engine, came with a 16" bar, and never cut all that well. I found elsewhere on this site the recomendation that you should use a bar length that is the same in inches as 1/3 to 1/4 the CC rating of the saw. On my Woodsman, this translated to 12", and I find the saw cuts MUCH better with the shorter bar - it does better burying the 12" bar than the 16" bar did with an 8" round.
Another note is that you can get Retrofit chain brakes for Poulan saws, at least it fit mine, and there were lots of other models listed - I found the part on E-bay, it was around $20, and IMHO is well worth it. The retrofit is a replacement chain cover with the brake mechanism built into it. I had to take the chain tensioner screw out of the old cover and move it over to the new one, and take the old hand guard off, as it is replaced by the manual trip on the brake. Works great in testing, haven't seen if it works "for real" and don't want to - I figure if you trip the brake while cutting you made a mistake...
Game of Logging is a class as I understand it, you have to go there and do the hands on thing, which I think is sort of vital for this kind of learning, books and videos help, but they only go so far. I don't know if there is "official" non-live training stuff available from them, but you can find some info on the techniques - try looking for "Swedish Logging Method" I haven't had any formal training in it, but even the little I've read has really improved my felling ability - I feel much more confident about being able to put a tree down where I want it (w/in limits)
As to your chainsaw, I'd go with the 50:1 ratio, or possibly a 30:1 - the old saws were intended for use with a richer mix than modern saws are, but todays oils are better. What I use, and think is worth the extra expense, is the little "one-shot" bottles that are designed to be mixed w/ a gallon of gas. Easy, reasonably foolproof, and give you about the right amount for casual use where you'll burn it up before it goes bad. I also look for the bottles that are clearly marked "includes fuel preservative" - I think it is vital for any gas that will be sitting for very long given the crap that the oil co's are pumping these days.
For the manual oiler, what I used to do (years back, and not using a saw all that much) was give it one stroke just before starting a cut, and then another stroke every 3-5 seconds while cutting. Until you get used to it, check your oil level often - when you are doing it right, you should have about a teaspoon of oil left in the tank when you run out of gas - just enough so that you know you didn't run out of oil first.
Good luck and work safe...
Gooserider