This can be a fairly easy and inexpensive DIY. But it does depend on basically 2 things as to “ease” of installation.
The first being where the well pump is located and the existing set up that needs to be tapped into.
Being in Virginia the location would need to be in a none freezing location. Our barn well, pressure tank, etc is located in a 4’ pit where the well was dug. It has concrete wall and a small building over it. The pit itself is quite roomy to work in and is covered with a 4X8 sheet of 3.5" solid foam insulation with sheet of plywood on top.
The freeze line in my neck of the woods in SE Pa is around 36" but I was only able to go 30"+= with some lines and have never had a line freezing issues. But all of my lines run in open sunny locations so even with a hard freeze winter the ground benefits from the solar gain from sunny days regardless of ambient temps. I would be very worried if the shallow lines ran under ground that received little to no sun.
Trenching to the plumbing location can be easy enough, If the plumping that you are tying into is located in a roomy workable location Because you will have to drill a 1" hole through the foundation X inches below the grade to get your pipe through. This will require a Hammer Drill and a 1" masonry bit. The drill can be rent and the bit purchased for around $20.
There are various size trenchers for rent in most locations. The ease of trenching 300’ depends on ground, flat, hilly, etc and what is underneath of it. The parts of NoVa that I lived and or spent time around is notorious for being rocky.
The first lines I put in around 1000’ worth I greatly under estimated how much time and effort the trenching would take. I rented a pretty good size machine also. It was nearly as easy or fast as the videos made it look. I also made the mistake of renting a machine on wheels instead of tracks. Which made getting up some small hilly areas problematic and strenuous. There is also a learning curve to these machines. “Tricks of the trade”.
The second 1000+ feet I trenched went much quicker using a machine similar to this;
http://www.gappower.com/Trencher-Rental-36-Deep-Vermeer-Chain-Type/item/TRE36
Most rental yards offer a very good discounted weekend rate, Friday afternoon to Monday morning. Contractors don’t work on weekends. Most people don’t just us “silly” horse people.
This is the standard pipe use for running waterlines on farms, 3/4" black poly. The less splices in the line the less likelihood of developing leaks. It’s cheap enough so having excess is not a deal breaker.
http://www.tractorsupply.com/tsc/product/100-psi-polyethylene-flexible-coil-pipe-3-4-in-x-400-ft
The various fittings needed to tie into the well line and hydrant are easily had and inexpensive.
The frost free hydrant cost around $50-75. Buy, use a brass elbow on the bottom of this to connect your pipe to. Nylon elbows are too easy to break/crack when installing and back filling.
No reason not to install an electric in freeze zone for tank heaters or future auto water. I would also wrap the riser pipe starting about a foot on the supply pipe around the coupling and up the riser. Just in case you encounter a long cold deep freeze period. The metal riser pipe makes for an excellent thermal bridge carrying the cold down the hole.
Use 12-2 “direct bury” for the electric line. It is called direct bury for a reason and does not need the extra expense and hassle of running it through conduit as others often advise. This comes in various lengths 25’,50, 100’, 250’ and up. It is on the pricey side of things. So you mostly will have to make one splice. Easy to do but do it well and use water proof splicing “kit”.
I made the mistake of placing one hydrant on the winter shadow side of a fence line with no heat tape. It is the only hydrant out of 6 that has frozen up on me during the odd deep freeze. I painted the pipe black to get the solar heat gain for the few hours the sun hit it. Makes a difference. At least I think it does. Kind of like horse supplements.
It is best to turn the water on and pressurize the line for at least 24 hours and check for leaks before back filling.
Back filling is a PITA. A tractor with a bucket makes it easier depending on how skilled the operator is. But back filling 300’ by hand is not that big a job. Getting the fill dirt tamped/tight over the line can be problematic. Filling a foot or so and then driving over it with a tractor, car or truck helps a lot. The “tighter” the fill dirt is over the line the better the insulation factor. But unless done REALLY well expect a certain amount of settling to happen over time.