Congrats! I'm just finishing the delivery side of my system as well, collection is working fine
Will the pump be running the drip irrigation in the garden or just moving the water up to another holding tank at the level of the garden?
We're using a shallow well pump from Harbor Freight, it's pressurizes the line and then shuts off automatically, when the pressure drops it starts back up and runs until it brings the line back to the preset pressure. You would need a garden hose type timer to shut off the drip, which would intern shut off the pump but that would work great. Here are my answers (opinions of course) on your questions.
1. I would look at a pressure type pump, I'm using harbor freight pumps, cheap and you can get a service plan pretty cheap to replace them if they fail prematurely.
2. A pressure pump wouldn't need the smart outlet. If you don't go with a pressure pump and need to turn it on/off remotely be sure that your "smart outlet" can handle the inductive load created by a pump motor.
3. Running a pump dry is bad, usually very bad. Most pumps won't last more than a minute or two with no water flowing through them. You'll have to figure out a way to stop the pump when the water is close to running out.
4. The same style flow meter should be able to be used on the output of the pump.