Brooke, If you read over the discription of what you are doing with your cub, it sounds just like what a fledgling does before it takes flight. Feel it out and when your confidence builds so will your altitude. You are the only one who can really answer whether you'rre ready.
The cub might be a little tricky on the ground, but you're already dealing with that. You may need to make coordinated turns with rudder and aileron. If that's a problem practice them on your trainer. I like your attitude. Its always better to be able to pack up your plane intact after a days flying but if you crash, make the most of it by trying to find out what went wrong. Be careful about being bored with a plane. When I get that way I always end up with trashbag of pieces.