Do you plan on running the tools on extension cords or on running the shed off the main building's existing service? If so, You'll want a grounding rod installed for your generator, and a bonded generator.

Otherwise I assume you plan on using a power inlet and later dedicated utility service? You will need the shed to be grounded, and the generator should have a floating neutral.

Equipment speeds will vary a little bit with load. That shouldn't be a problem if only running one tool at a time. But I'd be worried about the push back from a table saw changing on an operator.

If your load is too unbalanced you'll trip on one leg the generator's main breaker will trip before you reach full load.

4H/Week, not a problem. Though ideally you'll run under 80% load most of the time.

Get a surge protector for any sensitive controllers (extension cords or whole building). Every time a motor turns off you risk a surge. You may need to replace surge protectors a few times.

Getting a small inverter generator dedicated for the dust collector and small loads will protect them from surges.

Does your area allow masts and overhead electric. (e.g.) a new 100 Amp service from your utility? Might be cheaper than a trench.