Lots of information for you to digest. Brief synopsis of what I have seen looking at the information. Cow tag will take at least 1 preference point to draw. Buck tag is also valid in unit 41 and 421, the hunt code is DM041xxR. xx = the season you choose. Looks like you will need a preference point there as well. Keep in mind that I looked at this info very briefly and the preference point info may not be correct. All my information is based on the assumption you are hunting with a rifle. The info for archery and muzzleloader is in the stats as well.
I can't give you an answer for that one. Depends on which part of the unit you are planning on hunting. Some parts are probably better in the second season and some areas would be better during the third season. Maybe someone else on the site could give you some pointers without giving out their secrets.. You could also try to call the DOW officer in the area.
I have always looked for ways to save money and gain skills. I have the firearms basics covered so I rarely buy firearms these days. But I do watch for bargains. Sometimes a little TLC with simple tools will let you bring an old gun back to life without investing a lot of money. One such find was a side by side 12 gauge marked “W. Richards” It is not from the fine English gun maker Wesley Richards, it is a cheap knock off copy probably made in Belgium about a hundred years ago...