If you are planning to retire in 15 years I assume that you are close in age to my own age (51). You are correct that it is generally considered easier to learn to sail in a small boat. For people under 20 or so, I usually suggest learning in a sailing dinghy (a small light open or semi-open boat). But last summer I was an instructer in a class for people who were a little older and trying to learn in dinghies and I found that they spent so muchg of their time tring to keep the boats on their feet, that they really were having a harder time learing to sail than I believe they might have if they were sailing a small keel boat.
So my general recommendation for someone with a little less dexterity than the average sub-20 something, is to learn on a small, responsive keel boat, say 21 to 26 feet. Given your limited resources I would definitely suggest getting a used boat, but one that is in reasonable shape and comparatively simple. Owning a small boat you will be exposed to many of the sailing joys, challenges and maintenance issues that you will need to own a larger boat. But small responsive boats also provide a good platfor to really learn sail trim, boat handling and the the finer level of skills that are harder to learn on a bigger and less communicative boat.
You have not said where in the country you are located and the size of the lakes that you will be sailing upon, but there are a number of ways to go depending on the facilities that are available. Most lakes that permit boats, have launch ramps and there are sailboats that are designed to be ramp launched. There are some compromises involved in the design of ramp launchable boats and while there certainly are some ramp launchable boats that sail quite well, as a general rule, ramp launchable boats do not sail as well as boats with fixed fin keels. A couple exceptions to this, both of which are good first boats, are the S2 6.9 and 7.9, and the Schock Santana 23 (also called a 235 I believe) from the 1970''s and 1980''s.
My all time favorite recomendation for a great inexpensive first boat is the Ranger 23. These unfortunately were only commonly available (Ranger apparently offered a centerboard version but depending on who you talk to they never actually built one) in fixed keel models. Many lakes have simple hoist launching facilities (Which is easier on the boat since it is easier to do minor damage a boat by ramp launching it.) If the lake or river you were sailing on offered hoist launching, then a boat like the Ranger 23 would make a good choice. Other really nice small fixed keel boats for a first boat might include an number of C&C designed 22 and 23 footers (such as the Grampian classic 22). A little more expensive but higher performance are the Sonar or J-22. Both are boats that you could really grow into.
Another way to go would be to visit the areas where you might sail and see what are used as ''one design race boats''. While you may never decide to take up race boats, race fleets will often nurture and help a beginner learn to sail. Race fleets generally pick types of boats that are suitable for the sailing conditions. And you can often buy used race boats that are in good sailing condition fairly inexpensively. Of course if teh local race fleets are sailing really high performance dinghies then you might find your self in over your head but most fleets will be considerate enough to tell a beginner if their boats are unsuitable.
My current favorite learning to sail book is Steve Colgate''s wife''s book called something like ''Sailing for Women''. She does a really good job of covering the basics and then going on with good clear explanations of the more sophisticated information.
One really good way to learn to sail is to take a week long imersion course in sailing while on vacation. There are a number of sailing schools around the country that are located near resorts and you can take a week''s vacation and come back with basic sailing skills.
2) We are a bit away''s from larger cities and I have yet to find any place that gives sailing lessons
nearby. Not having the time to drive over 100 miles to get to lessons, any suggestions? And are
there any good books that I should be reading prior to all this for ideas?