Help! Where to start???
First off, while 28 foot Catalina is not a bad size for a first boat and a Catalina is probably a reasonable boat boat for lake sailing it is a little bit big to learn to sail if you are also going to be single-handing most of the time. Also since the Catalina 28 is a comparatively new model and from the nature of your questions, I am assuming that you are buying a new boat. I cannot recommend strongly enough that it is a really bad idea to buy a new boat for your first boat, both from a cost and from a time to get the boat properly set up standpoint. Getting a new boat sorted out takes considerably more time and skill than buying a reasonably maintained and prepared used boat.
As to your points to consider:
Starting out, if you want to learn to sail a boat well you definitely want a tiller on that size boat. Wheels do not have enough feel and take up too much room in the cockpit on boats that size.
Furling jibs are a convenience that come at a compromise. They are very popular because they offer a little more convenience in some ways than other ways of flying jibs. I have owned a number of boats in that size range, and have owned a 28 footer for the past 12 years that I frequently cruise and I personally consider roller furling a nusance and a safety hazard for single- handing on a boat that size but that is a pretty unpopular opinion.
I strongly prefer the reliability and conveience of an inboard diesel. On a lake you might get by with an outboard if you are a pretty handy mechanic.
There is no way that I would recommend that you buy a new boat. Setting up a new boat right takes a lot of time, money and skill. For most people a used boat makes a lot of sense, especially for a first boat. After all if the first owner blew it you don''t have to buy the boat. If you make bad decisions, it is your time and your money that gets lost.
As to the next boat, hopefully the experiance of owning your own boat will teach you a lot about boat ownership. While you may indeed end up buying a Hunter 450 or Catalina 470 ten years from now you may also learn a lot of lessons that would steer you towards other boats that may be better suited to your goals.
Good luck and feel free to ask more questions as things progress. This is a great BB with a lot of knowledgeable people.