Hey Vince!
It's very exciting that you are looking into learning how to sail.
Part of the answer to your question will be determined by what you consider to be "competent".
Competent could be that you are able to walk onto a boat and sail it efficiently as part of a crew, doing one or two specific jobs. It could be that you are able to rig and sail a particular boat from point A to point B and survive the journey with no damage to yourself or your boat. Or competent could mean that you could step onto any boat regardless of make or design and sail her as fast as possible, safely and with no damage to yourself or the boat. Like anything else you definition of competence will change as you learn more and progress in the sport. You can learn the basics of sailing very quickly but pretty much just takes time to accumulate the experience that will allow you to deal with the various situations that are possible.
Regarding difficulty, it's really about "tiller time" the amount of time you get to spend time on the boat sailing. If you do not have a boat of your own here is what I would suggest:
The inexpensive non-professional training route.- Find a friend with a boat and ask them to teach you how to sail.
Or
- Pack a small duffle with your lunch, sunscreen and raingear. Go to a local yacht club or sailing club very early on a Saturday or Sunday morning, 6am early, and walk the dock asking boats if they need any crew for the days races. Or go on Wednesday night for the "Beer Can" races and do the same. Note - this will be baptism by fire! These guys are going out to race and can get very competitive, don't ask too many questions, do what they tell you to do and absorb as much information as you can!
OR -- The professional training route:
1- Find a yacht club or sailing center, maybe even the park district, in your area that has an Adult Sailing Program. These programs will usually be based on the US Sailing learn to sail program curriculum
http://www.ussailing.org/. These adult sailing programs are usually held in the evenings or on weekends to help coordinate with the common weekday work schedule. The time of the class will usually be spent 30% in the classroom and 70% on the water. Courses like this usually use two person dinghy's with a Jib and a Main sail. As the course and your ability level progress you may be able to jump into a single-handed boat like a laser but in the beginning the two person boats have the benefit of two people helping each other remember what they learned in the classroom.
2- After you have passed the course many programs will have their boats available for you to rent, do that as much as you want and can. Practice what they taught you, you will gain confidence very quickly.
3- Pack you duffle and walk the dock as mentioned in the first option above. With the knowledge and experience you gained from your adult sailing course the baptismal fire will feel more like bath water!
4- Try to sail on as many different boats as you can. If you get on a boat by walking the dock and have a positive experience stick with that boat for a couple of sails and then ask the owner or others on the boat to introduce you to other boats that you could sail on. If you explain that you are trying to learn as much as possible they should support it 100%.
5- Depending on what you want to do with sailing it may be time to look at getting a boat of your own. In that case you first need to determine what type of sailing you want to do and where you want to go.
OR
Buy a boat, put her in the water and see what happens!
I would suggest reading the following books:
"Start Sailing Right" by Derrick Fries
"Basic Keelboat"
both available for about $17 each at
http://store.ussailing.org/listItem...&SubCat=START&SubCatDesc=Starting&Search=Link
Also - the US Coast Guard Auxiliary has a book called "Boating Skills and Seamanship"
that will address more general boating knowledge.
Hope that helps a bit,
Brian