Guardian
1. Not really, though you could form a fleet of your guardians so you can use a hot key to select them, and then just hit the button.
2. Each ship can only have one guardian shield buff at a time. However, multiple guardians will cover eachother, allowing they to take some of the damage for the first gaurdian. However, you'd need to be in a massive battle to ever need more than three at once.
3. A fleet with about 1000 fleet points can fit inside a guardians area if you keep them really close together. Mainly used too make the "battle ball" where illuminators cluster around a gaurdian(s) with a mothership nearby.
4. Often a good choice, though repulsion field is one of the best ways to protect carriers and to stop the rare Heavy cruiser spam.
Subjugator
1. Infinite Void nailed it. I try to keep one for every cap ship I have. Not worth using on frigates, save maybe carriers.
2. Depends on what kind of enemies you are fighting.