I have directed so many new folks to read the old threads, but I know it is a bit intimidating. there are 600 plus pages of threads, with probably 10-20 posts in each thread. so I can understand it is a bit overwhelming. but you need to dedicate 2 hours a night of reading each thread going back in time for the next 2 weeks. all the answers you will seek are about 24 hours of reading away.
I always try to encourage folks to get a list similar to hotrods and do the front of thier home and a friend or family member. clear c-9's, run the cords, timers, learn to put all the clips on the same side, etc.
It is way cheaper to buy a case of incan c-9s at a 1000 bulbs than a case of 500 led's, so maybe start there. 1000 ft spool of 12" spacing
I would get a 6 foot or m26 little giant ladder on ebay, that will do 80-90% of everything you need to do, and maybe a 32' or 40' extension ladder when you sell a job that needs it.