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I think you'll find life in Riyadh very different to life in Dubai. I will try to answer each of your questions in turn.
With regards to driving, if you have a UAE driving licence already, it should make acquiring a Saudi Arabian licence easier. You will however, be required to take a couple of tests. It is advisable to contact a local driving school to assist you with this. Maybe your employer can recommend a company that has been used by expats before.
When it comes to getting yourself a car, take a look at this page of Buying a Car in Saudi Arabia for more details - it is quite a complicated process !
Even though, life on Western compounds is less strict than elsewhere in the Kingdom. It is still illegal for unmarried couples to live together. While there is won't be the Mutaween (Saudi religious police) on hand to watch you within a complex, it is still not a good idea to try and consquences for breaking the law in Saudi Arabia are severe.
While alcohol is illegal in Saudi Arabia, you'll find that people do drink within the Western compounds.
Take a look at our Expat Arrival's Saudi Arabia Country Guide for more information on what to expect. I think the page on Culture Shock could be particularly useful.
Good luck!