"the biggest hassle may be that you have to maintain two separate wardrobes: One casual, and one professional. "
I must be dense. What's living aboard got to do with wardrobes? You put on a three-piece suit to work in an office, do you lounge around at home watching the tv or mowing the yard in the same wardrobe?
You jerk burgers at McD's and put on a different color "suit"...Do you wear that one at home too? Crash pad, crib, or boat?
If you need "working cloths" it doesn't matter if you're a banker or a painter, or where you live, you still need work cloths versus the fuzzy bunny slippers that some folks can wear all day.
And hey, do you have any idea what those genuine antiskid marine grade fuzzy bunny slippers COST?!