I have to agree with the other posters, that you need to have a lot of experience to know what you really want and need. I don't feel you can just think this through, but have to experience it. And that comes with time and trial and error. I am not against buying new, but I would look for something built and sitting on the lot. There is a lot more flexibility of the dealer to unload inventory, than just be the ordering platform. If he has it on his lot, he either owns it or is paying floor plan interest on it. That is an incentive to deal.
If you have 2 years to retirement, jump in with a used unit and start working on your "Must have" items.
Good luck in your search.