Normally after count time and before dinner

The federal sentences come with 15% goodtime credit going in.  If your fiancé stays out of trouble he will serve 28 months. If he has an alcohol or drug problem he might qualify for RDAP, which if taken would cut 9-12 months off the 33 months. Ask the Inmate about RDAP.

It's not a hotel, they process at the pace that they can

maximum security

Usually, new inmates must go through orientation. That happens within a week. Inmates that communicate well with their counselors and case managers can sometimes convince them to get family members approved faster than normal. It depends on the inmate's persistence.

Life inside prison is like the movie "Groundhog Day". Every day is the exact same as the day before. Boredom dominates the menu. The only way to sanity is to get into a routine you can live with. You have a lot of time to think and getting into a routine takes you away from lamenting on your situation and more towards feeling as though you have a purpose and some hope for a better future.

Inmates must go through a short orientation program before the privileges are activated. They can, however, receive letters or postcards from InmateAid and they can write back.

No, to either. This is absolutely forbidden.

Usually, about one week. The BOP sets the new inmate Admissions and Orientation on Wednesday. If the inmate gets there on a Tuesday it's only a one day wait. 

You can try calling and see if a staff member will do it for you. It is against the rules in most places, but sometimes if you're nice they will make an exception. The alternative is to write them a letter or postcard to let them know what's up.