The problem is finding where the cable has failed if its buried.
If you know within a yard where the problem is, digging a big hole and doing the repair may be only slightly annoying.
That may be possible with equipment and expertise you probably do not have or can get at a reasonable cost.
So if there is voltage at one end and nothing at the other end.
What do you do next ?
With a device known as a "TDR"
I don't like the generator and inverter at PV array idea.
You live in Alaska, and have an all-electric house, including heat. Kind of like the California of the future, when gas hookups are banned (think of someone in Tahoe during a power outage, if perhaps they weren't allowed propane either.) You'll have to walk 500' uphill in the snow to restore power, can't call the utility to do it.
I'd rather have a diesel generator at the house, and battery inverter. During a storm, generator can run occasionally and inverter keeps power going 24/7. "Combined Heat and Power", only 1/3 to 1/2 of energy from fuel generates electricity, so capture and use waste heat.
If electronics fails, you still have diesel for a heater.
This is one of the benefits of using AC coupling, GT PV inverters at the array (an AC power run from house to there.)
Yes, if you're looking to move high voltage AC a long distance, your choices are thick wire or honkin-huge transformers that can convert all 3 legs (hot, hot, neutral) to a higher voltage and then another one at the other end to kick it back down. The big question there being is the expense of 2 honkin transformers AND 500+ feet of smaller copper wire rated for over 600v saving you anything over just running really thick aluminum standard supply wire.
My math and internet shopping has said yes, transformers are cheaper than larger gauge wire.
We do have to consider whether transformers have a problem with the environment. Ventilated dry transformers would have windings and laminations fairly exposed. Cheaper ones are aluminum not copper. Are they OK there? Maybe OK inside the culvert walled earth-sheltered electrical vault?
High voltage "pig" transformers have been suggested. I think 960V will be sufficient for this moderate wattage system to make wire economical.
Possible issues with 12kV transformers:
While above ground can be air isolated, wires are subject to damage. Underground will require much better insulation than +/-480Vrms.
12kV will kill you more dead that 240V. or at least, the "scared straight" videos of our training feature amputees.
12kV, if it discharges in an arc, produces X-rays.
I think these transformers are oil-filled. That has its plusses and its minuses. Improves environmental sealing and power handling. But, oil degrades especially with electrical discharges. Big transformers get their oil lab tested and changed. Maybe the little ones are "sealed for life" and recycled when their time is up. Failures can be fires.
I don't know how much danger of damage to a buried line in conduit. I've had weak glued joints come apart. Cheap sprinkler pipes in shifting earth. PVC conduit with very loose tolerances, isn't mechanically tight when I try to glue them.
Is it possible to get a flexible reel of conduit with wire already in it?
If wire was backfilled with oil (check compatibility of insulation), that would exclude water.