Hi Cris and welcome to the forum. I can answer some of your questions, I'm sure others will be along to do the same.
- The draggie is an excellent intro to cruisers, not too heavy, not too big, and handles far better than she has any right to.
- Are you looking at the custom or classic model? I'm guessing the classic since that resembles the HD fatboy more.
- As long as the battery's good she can sit for 2-3 weeks with no problems, but it's probably a good idea to get a charger. Removing the battery is quite easy.
- Now, commuting: you can certainly use it for that, again, along with the handling, it' a suprisingly good commuter. Make sure you only do it in dry weather though, as the rear monoshock can get corroded and snap in two.
- I'm sure your height will not be an issue.