Should I enlist as a 35M (HUMINT) before reclassing as a 38B (Civil Affairs)? If so, what should I have on my contract (airborne, DLI, etc.)?

Your contract should be clear and to the point.

If they don't have it spelled out exactly that you are a 35 Mike and that you have Airborne School on it.

They can't say oh, maybe later? Do not sign the dotted line if it is not spelled out exactly the way it should be.

Another consideration would be to go into civil affairs from an Army Reserve unit. I know that 10 years ago, I remember seeing privates walking around my civil Affairs battalion. They were not all specialist or higher. There are various civil Affairs units throughout the nation that are airborne. That way, you could still be Affiliated and go to school. You could even join ROTC and possibly become a commissioned officer by the time you're 23 or 24. Civil Affairs units are usually deployed every other year it seems. So you won't miss out on much if you are in a United States Army Reserve Civil Affairs unit. If you score well on the Defense Language aptitude battery, they may even send you to a school for a year to learn a language based on the units needs. Depending on where your unit is located, is depending on what language they may allow you to have. Being proficient in a language can allow you to make $300 a month or more depending how many languages you have been certified in. Just stuff off the top of my head. I'm sure there are many other civil Affairs people who could help you.
MAJ (Join to see) CPT Pedro Meza COL (Join to see) CSM Charles Hayden SFC Joe S. Davis Jr., MSM, DSL SFC William Farrell

The two have very little to do with each other. Psyop is probably the closest thing.

Jeremiah, any skill will help you. Civil Affairs usually wants to bring your civilian or other than military skills into the picture. The MOS you chose is a great one and anybody would want you with being a 35 Mike. I would say to keep up on current events, read the newspaper, Read International world news and listen to National Public Radio or BBC World News. Since civil Affairs covers different parts of the world, it would be good for you to basically be someone that likes reading or watching the International news so you have better situational awareness. Being a history buff will also help you. If you have the History Channel or National Geographic Channel and watch past historical events or battles, this can also help you. Studying up on the Middle East Wars would be very helpful if you are going to be dealing with the Middle East as your emphasis. I wouldn't worry about it, just make it a hobby.