Re: Boat for Single-Handed
I would lean toward learning on the smaller lake. However, down the road you will find it wonderful to have the boat nearby. It is great to be able to pop down to the boat for an evening onboard. That is the kind of stuff a sail-resistant wife likes (at least mine does). And without the hour drive you can be more selective what weather you go out in. If you trailer a boat to the lake expect at least another hour to get it rigged.
Remember there is a steep learning curve in sailing, AND there is a steep learning curve in boat ownership. Doing both at the same time is more difficult.