Yes always tried to wash my one pair of shorts every night but only if I was sure they would dry overnight. And your cycling shirt will dry out generally quite easily. Avoid cotton.
I would recommend cycling shorts with a chamois inside rather than the thicker padded things. For the first time I tried them and getting hot and sweaty could not get them dry while riding and ended up like I was wearing a wet diaper - first time I have ever had saddle sores. Plus these are harder to dry overnight. But I guess like lots of these things it is all personal choice and what has worked for you in the past.
Good luck and wish you well. My next plan is Orlando to Vancouver in Spring next year - can't wait