Let me try my best at answering your questions.
As far as parking, it is very limited on campus. As far as I know, it is nearly impossible to get a parking pass in one of the university lots; in fact, I think you have to be a certain distance off the bus line to even qualify. I believe there are monthly passes available in the city ramps, but I'm not sure what the pricing/availability is. You'd have to check on the city's website, there would probably be some information there. What some students do is contact downtown apartment complexes and see if they have any parking available, which many often do. To the best of my knowledge, this will typically range between $50-$140/month, depending on whether it is underground or outside, location, etc. I also have seen this type of parking advertised on craigslist when I've checked previously.
I live in Middleton myself, and I should be a lot more diligent about trying to get a monthly pass at an apartment complex. I park daily either in the city ramps, purchasing a daily pass underneath the business school, or parking at the meters under the business school, and this ranges from anywhere between $7 and $12 a day depending on my schedule. It ends up costing me about $200 a month. I definitely wouldn't recommend this if you are going to be living alone, but since I live with my fiance, my portion of the rent is only $460, so I justify it by saying it is similar to what I'd be paying in rent if I lived on my own. Personally, I love living out of the downtown area, but I am also a bit older so I think that plays a part in it. Many areas in Middleton are great. I'm not too familiar with the Arbor Hills complex; I know there are students that live there, but a few years ago when I lived in a different area of Middleton that was closer to that area, it had a shady reputation. I would stay away from South Park Street and the southwest side---those are both some of the more unsavory parts of Madison. The east side has some unsavory areas as well, but also has a lot of nice areas that are newer. I'm just not as familiar with those as I have always lived on the west side or in Middleton. Living out of the campus area has its benefits--for example, right now I have underground parking included, a washer and dryer in our unit, a pool and a fitness center. Additionally, my fiance parks his car outside for free. Without knowing your budget it is hard to direct you to places, but if you'd like send me a private message with your budget info and I can try to direct you to some places I have lived on the west side/Middleton. Keep in mind that many of these places start around $700-$750 for a one bedroom. I also think it might be worth it for you to check out some of the complexes near Hilldale.
There are a few different schedules that you may have. When I was a 1L some people started around 8:30/9 a.m. and with 2-3 classes per day would be done around 3:30 or 4. I was in a later track both semesters and started around 11:00 a.m. and with 2-3 classes per day, ended at 7:40 two nights a week. So, it varies. I was more of an early riser (by early I mean by 8, lol) so I was able to get in a hour or two of reading before my classes started. Unless you have a compelling reason why you need a certain schedule, there really isn't anything you can do about what you are assigned. While it sucked to have class till 7:40 twice a week, there is no way I could have survived starting class at 8:30. You will adapt and get used to whatever you get. And you should be getting your schedules the last week of July, I believe.
Hopefully this helps. If you want more info about the housing, just let me know.