You're doing excellent as-is. I wouldn't worry about it too much. You're not "going easy" on yourself.
And no, free weights aren't the same as the weight indicated on the machines. Before bikes my BIL tried to help me with gym plan stuff, and when he got me off the machines he told me to ignore what those said. The free weights in most instances were more difficult.
Reason is the machines might simulate a range of motion, but they still don't force you to use stabilizing muscles to perform the proper form of the motions. That's what he said at least. I've no idea if that's totally accurate, but it made good sense to me at the time.