1) & 2) As fields are not stored internally in a position relevant way I'll say that there will be no difference between the position of the index fields in the table. However I tend to put indexes in the first fields by convention.
3) Rebuilding indexes is a heavy task that will have a negative impact in your app's performance, so it's a good idea to launch rebuilds out of production hours. The newly inserted rows in your DB are below 3% each day, so your searchs will lose about a 3% in performance each day until you rebuild your indexes. This is not such a big deal if you rebuild them in a daily basis.