Hi Mallow
I have about a 100 trees in the ground now, and I've had lots of problems trying to water them. When I first planted them four years ago I put in a drip system with automatic timers to water them when I wasn't around.

The ground squirrels in my area thought it was great idea and chewed holes in the pipe so water would drain down their holes. I lost thousands of gallons of water from my holding tank before I knew there was a problem. They chewed holes big enough to insert a finger into the pipe. I've used traps, poison, and have shot them on sight, but haven't put a dent in the squirrel population.
After that, I shut down the system and watered the trees by hand, one by one, with 5 gallon buckets for 1 and half seasons. Using two buckets that I alternated I could water the whole orchard in about 45 minutes.
I finally laid a system with hard PVC pipe with bubble heads to flood irrigate each individual tree swale. I tried the automatic timers again, but our well water is silty and the bubble heads clog easily.Some trees would flood while others were bone dry. Even in-line filters quickly failed because of the silt load. I finally tore out the timers and put in hand operated valves that I open and close myself. My holding tank is about 200 vertical feet above the trees which should give me about 80psi. I found that I could only water about 20 or so trees with that amount of pressure and get flow out of the bubble heads. I now have 5 valves to water my 100 trees, about 10 minutes per valve. I walk around to each tree during watering to make sure that the bubbler isn't clogged and water is coming out. I also have to quickly plug any squirrel holes in the tree swales to prevent all the water from draining away.
If you don't have any rodent problems in your area, then I think the drip system would be great. Be prepared though to monitor it very carefully to check problems before they become a disaster. If I had, I wouldn't have lost 6 months supply of water.
Michael