@Deacon211 I just gotta say, thanks for posting in the BMS topic and giving us a glimpse into the life! I enjoyed the heck out of your description of the logistics of AAR planning, and you explained it in a really simple way that made it perfect for dummies like me. Plus it was a lot like the parts in a Tom Clancy novel (Red Storm Rising, for instance) when he delves (semi) deep into the technical details of something for a few pages- thoroughly enjoyable and explanative. So thanks! 
For me, it’s the most rewarding part of it! That, and trapping on the boat. But I’m better at AAR, for some reason. Start with the Hornet, because that takes trimming out of the occasion. Keep the motors spooled up, make small corrections, and listen to everything people like Deacon say and after a few nights of practice something in you will ‘click’ and it will become easy for you. The best part is the level of control of the airplane that you achieve translates to everything else too, since it’s really just precision formation flying. The best part is once you get it, it’s kinda like riding a bicycle in that you don’t lose it too much when you are away from the sim for a few weeks. Something something neural pathways in the brain or somesuch… 
ETA: Just to caveat, I’m talking AAR with a probe and basket. The way the USAF does it is just… weird and unnatural. I’m not going to say I’ve never done it in the A-10C or F-16, but maaan the F-16 is hard. It’s behind you, and I can’t see the lights very well at all in VR. YMMV, but I haven’t got the boom and receptacle thing figured out quite yet.
I actually went from learning with the Hornet/Tomcat, to trying it with the Harrier and was able to plug after the first couple attempts. I wouldn’t say it was easy, but it was certainly no harder once I got the sight picture. The throttle response is sweet, which gives it a lot of points IMO.
In DCS, I’d rank them something like this:
Hornet: Easy mode (relatively speaking, AAR isn’t)
F-14B: Fairly easy in ‘bombing’ mode, A is harder with those engines that take a day and a half to spool up and compressor stall if you’re not careful (“Boom. Boom. Boom!” ‘Oh sh-’)
Harrier: Easy to handle, great response, can’t see the probe. Use the Force, Luke. 
F-16C/A-10C: It can’t land on a boat, and refueling tackle is backwards. Why would you want to fly that?