Welcome! Don't apologise for asking questions, that's one of the reasons for the board existing.
The right hand winding hole on your clock is for the time, the left hand one is for the strike. If I remember correctly, on these clocks the right hand wind is anticlockwise, the left hand wind is clockwise. I may be wrong, so just try it and you will soon find out.
As for how much to wind it, just carry on winding until you can feel it stop, you won't be able to wind it further. You can't overwind a clock (unless you took a wrench to it!) - overwinding is an old wives' tale. If you don't wind it fully it will not run for the full time it is supposed to.
It will almost certainly need a good cleaning and servicing. I am not sure if you are planning to do this yourself - if so, you will find lots of people here only to happy to help you through it. If you are going to get it done by a professional, then make sure it is some one reliable. You could contact your local chapter of the NAWCC and they will gladly help you find the right person.
Be warned - clocks are addictive, once you've dealt with one you can't stop! But you'll meet a lot of good and helpful people along the way. Good luck.
JTD