I occasionally take my bunny for an excursion into my sisters fenced garden, he is confined to an xpen and is watched closely the whole time (usually a few hours). Alfred is a pretty confident sort of bun that likes to explore and run and really seems to enjoy his time in the garden. I think it depends on the rabbits personality. I would feel a little like I was depriving him if he didn’t get an occasional foray outside my apartment, but I know there are risks.
Last time we were in the garden he got to have a run outside the xpen in a harness and leash. I know this is somewhat risky and a bit controversial, and is not something I would advocate without weighing up the risks and benefits. But as I said Alfred is quite confident and really likes to run. The harness didn’t bother him, and he loved being able to run and explore. One thing I did do was tie a piece of elastic (the type used for sewing, approximately 1.5 cm wide) to the handle of the leash, and then tied a loop in the other end to use as a handle. This meant he wasn’t jerked back so hard when reaching the end of his tether, so to speak. It seemed to work really well.
If I were you I would try taking Dorothy outside if you think she would enjoy it. Just take precautions and be vigilant.