JD, welcome to the forum and world of riding. I was like you; in my forties and waiting till my kids were grown until I started riding. I think you make very good judgments in looking for lessons and avoiding the crotch rockets. As far as lessons go, the local DMV or D.C Police should be able to inform you of what is available in your area. I would make sure that the riding school is certified with certified instructors. My school started on a Friday night and ended on Sunday afternoon. I would be wary of anything shorter. In Massachusetts, if one completes a certified riding school, they do not have to take the road test for the motorcycle endorsement.
As far as good starter bikes go, I won't recommend a specific model, but I would start out with an upright seating, cruiser type model in the 650-900 cc range. As Hyksos said, if you really enjoy riding, you will probably quickly outgrow that size (although some remain satisfied with that size and that is fine) so I wouldn't spend too much at first. The exception would be the Harley Sportster 1200. This particular bike isn't too bad for a beginner. The Sporster also comes in a 883cc model but this model is seriously underpowered. My wife's cousin and her husband owned a Harley dealership and she said she would absolutely refuse to sell me an 883 for that reason, and that a 1200 was fine for a beginner.
Seat height is also very important, especially for the beginner. You don't want it too low or too high, however if a choice must be made, lower is better. Your feet should be able to rest firmly on the ground when the bike is upright.
I do feel that the 250cc size is too small for a beginner if he is going to be riding on highways or open roads. It is fine IMO for around town, but out on open roads I don't feel that you will get a good feel for a bike with an engine this size.
Let us know how you make out.
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