So a few things.
If you upgrade service, you probably need to upgrade wire. That means trenching and thhn or some sort of UF wire. When you break out a trencher- it just gets expensive. Looks like your run is 50' from the source. If they just trench a new line, lay the new pipe, upgrade the primary and then re-power the disconnect- I can see it taking a day and a half for 2 guys.
If you were able to go overhead. the cost is about 1/2. When we can, we put up a single pole next to the home, and swing fresh power from the primary pole down. Now we only need to stub into the home and the box, no trench. This does not work everywhere, but if you want to save money with electric- keep it out of the ground.