Heyriddle - You are right, it is very time consuming! Add to that the regular college applications.....
We made a checklist for each college, ROTC scholarship app, USMA, nominations sources that simply lists the name and then under it a list of items: transcript, SAT scores, recommendations, application, etc. It is all on 1 piece of paper so you can see at a glance what is left to do.
We tackled the "easy" stuff first - the application part, scores, etc. Have a stack of transcript requests, and a list of transcript requests for the colleges that have no form, and will be delivering those to guidance next week.
This weekend he will make a list of exactly which teachers he needs recs from and will develop a letter to give them to explain what he needs, and then ask them if they would like to write the rec for him.
DS is working on essays, first the ones that were "easier" for a few of the colleges, then the ROTC, and now working on USMA, which will also be used in part for the noms.
DS also wants to play his sport in college, so we are in constant contact with 6 different coaches, updating them on schedules, etc.
I think I get more nervous about him getting everything done in the next few weeks than he does! And yes, this college search has taken more time than my older 3 kids, and hopefully will work out the way DS wants in the end!