well my procrastinating expertise tells me to just do little bits, unless your retired or have a lot of free time, 2 months is roughly 8 weeks, which equates to 16 working days ( weekends) allowing time for ordering etc, then we are coming into spring and honey do's which if your married you need to keep the dungeon master happy too
. so there will be other tasks besides your build, so I would think that making a list and putting down realistic time frames for each task , now you say brakes but I don't remember if you were upgrading to discs etc, if not I would say all 4 brakes is reasonable in a day, but the prep and painting that it sounds like you want to do is a weekend in itself so say 1 weekend disassembly and painting and then 1 day reassembly, so 3 of 16 leaving a balance of 13 etc... but I always plan on things taking twice as long, so it leaves you 10 then there is your budget.. me everytime I save enough for the quarter patch panels etc something comes up, and out the money goes, I don't know what your situation is but you would save time getting all the stuff ordered too... if you can,
The main thing is your goal is to attend the run, and then what is the point of going on a cruise tour with no jingle in your jeans? so money is the other issue, priorities my man priorities!!!
I dig your cutlass BTW, I have loved that body style ever since building the old hurst hairy olds as a kid...