Lanette, I completely relate to your plight with the gears! My husband, a bicycle expert, says older bikes that haven't been well maintained shift badly. I had a good quality bike that I had purchased used from a friend many years ago. I never could get the gears thing down (it had 18 gears.) So my husband helped me find the perfect replacement bike for my needs and I LOVE it. It is a cruiser with 3 simple gears on the right handlebar marked (1, 2, 3.) I ride on paved trails and neighborhood streets so this is all I needed. Also it is a belt drive so it doesn't need to be oiled or get rusty, it is silent and doesn't squeak! My husband also comments that "I think the main thing if somebody has trouble shifting is to get the internally geared hub." Hope that helps.
By the way, for other reluctant riders who are worried about their weight... I have been riding even at my highest weight of about 365 and I am in my late 40's. It is easier on my joints than walking. Just make sure that your seat is at a correct height for you. If everything is adjusted correctly for you, you can enjoy without pain.
Oh and invest in a wide and comfy seat, upright handle bars, whatever is best for you! And buy a good helmet!
Good luck,
Carol
FYI: I have not yet been sleeved, it is coming up on Sept. 23. I hope as I drop some pounds I will be able to ride more / farther!
A pic of my bike