I have some experience @your conundrum. An overhaul like this might take 1-3 months to do all@ once. Along with maintenance every 6mo.s to a yr.
Its up to yourown understanding of your goals& posible need fore that Easy Street you mentioned.
I hesitate to Actually give you Definitive advice on scheduling.
But, you can ignore me if you want; especially if at some point in the future, it becomes a hoursecrap solution for your efforts.
Make a midsized. Solidblock. 1st attempt @ maintenance. Give it a troublshooting period..
Rinse/Repeat & try to get things squared away in 3or4 reps.
Dont be afraid to extend the troubleshooting period to add additional content. We're not going to abandon you for getting your shit straight, if you'll pardon the vernacular..