Welcome to the forum.
Most people new to sailing don't start by buying an entire fleet
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Learning to sail is one of those things. The necessary skills to get out on the water aren't that difficult to acquire - some people manage to figure those out on their own. Others read up a bit first. If they are smart and cautious, they keep the wind in a range where things are easy to manage, say up to 8 knots (9mph) and don't head for waters full of traffic or challenging (tidal or river) currents. Within those parameters things should be forgiving enough to allow self-study.
Having someone talk you through this, and demonstrate the maneuvers does make the process go more smoothly, but it's going to take someone more than a few minutes of their time. A long afternoon for the barest minimum, I'd say. Depending on how much handholding you are after, figure the equivalent of a full weekend, perhaps spread out.
That would get you to the level where you can get your boat from point A to point B under sail. You'll quickly find that the combinations of wind and waves are endless and that learning never stops. You'll always learn something new, and that's one of the reasons people find sailing fun. Most of that learning you'll do yourself, but it doesn't hurt to spend some winter evenings reading and re-reading whatever books and other materials you can get your hands on. Also, at some point, past basic learning, reaching out to tap some experienced sailor for additional input will be useful.
Good luck to you in finding someone in your area. Have your checked on
http://daysailer.org whether there's a DS fleet in your area? In the meantime, you could do worse than going and reading through the older posts here on this forum. Not all are about centerboard cables and motor mounts.
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