Singlehanding a 41' Hunter DS?
A new hunter 41 will be easy to singlehand once you get the hang of it. I went a similar route 18 months ago with a 1985 Hunter 40 (money is an issue!) and single hand frequently.
Your plan for ASA courses is sound, that's a good start. I spent a year taking courses and then renting a variety of boats for daysails from the place that gave the courses - sailed everything from a Watkins 27 to a Beneteau 39, including single handing. Helped immensely but I found that the first 20 trips on my own boat was the real education.
On my boat the most important things for single handing are the autopilot and preset dock lines for entering and leaving the slip. If I could add one thing it would be an electric winch to help raise the mainsail - but if you get mainsail furling then not so much of an issue. I don't understand all the comments about bowthrusters - with a little practice docking becomes second nature, even singlehanded.