So what I do, is I use the boot to do a reverse area order clip into High St. But with that clip, you can clip in but not out, so that is why I clip into the garage as to replicate as best I can what would be done in a any% glitchless or an AFT run. I did the same thing with back gardens so the goose gets thrown out of the house(it is possible to clip there) similar to how it does it in an AFT run. Basically, I want the first tasks of the run completed, while the game progresses as if it were being played casually.

For your second question, we shall take Pub for example. The bell return can't be done without entering the pub and completing the "get into the pub task". The exact same with model village. So tasks such as these must be fulfilled to finish any run ending in bell return. Now to answer your first question, on how High St and Back Gardens can be completed as such. The High St garage door can be clipped through using a boot, as well as the side exit of the garage; the way the shopkeeper gets out of the garage normally. For Back Gardens, I took the same boot, went to the right of the purple plank(from the player view, not the goose) and kept attempting to phase through the fence until I succeeded. I intend that this run is not glitches, for the reason to complete only the tasks you listed above.

While I was busy grinding, I found out it is possible to exit High Street as well as Back Gardens, how the game intends you to exit), while completing not a single task! But since Garden, Pub, and Model Village have a task completed upon entrance, the game can't be finished(as in completing the bell return) without completing a task. After I made that conclusion, I realized that the areas with mandatory entrance tasks all have that task on the top of that area's to-do list. So May I suggest adding a category in which the runner's goal is to complete every first task as well as the bell return in as little amount of time? I apologize for my lengthy entry, I like writing.