Mine is a month to month entry, though I often do multiple declarations at a time which generally follows the same pattern below on a uk schedule. I also have no issue putting multiple horses in the same race, not uncommon for me to have 4/5 horses in each of the classics.
2yo - I start at the end of the jump season usually opening around the time the Chesham 7f is run and aim to have 4/5 races in all horses before considering them for export. I cover pretty much all the group races, and finish with my whole stable going into the November races, the two bc miles, the criterion 1m and the G3 6f and the 1.2m St. Cloud.
3yo - start with the G3 1m's just before the 2000 guiness, or at the guiness themselves for the milers, then onto the st James Irish 2000 and the few French g1, the girls do the 1000's coronation etc and clash with the boys later in the year, my 3yo's usually get 5 races before October when i rest them again looking to export. Harder on the sprints who get the Alberny early and other g3's up to the July g1 and the g1 5f the name of which escapes me. The 1.4's do the classic trials early before going to both the derby and Irish derby, then Grand Prix de Paris and one other, usually finishing around the st ledger. The girls the same but on the oaks path, Irish and Yorkshire etc.
4yo - I try to get 3 flat races on each horse early, looking at the g1's that are easy wins, so Falmouth, Sussex for the milers, juddemont and Irish champion for the 1.2, the 1.4 take a path to the arc. They often meet my own 5/6yo's if there not all chasing by then. They then rest until towards the end of the year where they start jumping, typically I hit the Christmas card whilst they are still 4yo then Cheltenham and aintree, so they run the later early in their 5th year.
5yo - usually here I split them between jump and flat, based on how they did at 4/5 and a little stat view and gut feel. 90% of my horses peak at 5yo so I go after pretty much all the flat G1's and hurdle/chase g1's. Always the hardest year to manage.
6yo - I stat check early year and repeat the 5yo approach some flat horse may do both codes or switch to jumps.
7yo - usually do a final export early before year end and retire most a few distance chasers will be kept until 8, anything in the 4m range until at least 10. My flat only horses are usually done in their 7th year.
Not sure if that helps or not
Josh
