1998 500 Dancer, 3196s, rip out, total rebuilds of both including new heads and re-install by Ohio CAT, $55K all-in in 2006 prices. There is a nearly two-decade old thread somewhere here on it from back then with pics if you search under my posts.
My experience has been that you can almost always count on (sometimes very dense) fog east of Mackinac to the Rogers City area in early mornings. Everyone is transiting in two opposite directions a few miles offshore. Know how to use your radar!
~620 NMs. If you pressed it hard, like ~130-180 NM per day, you could do it in four solid sea days. Grand Haven to Leland (~150 NM), then Alpena (~180 NM), then Port Huron (~150 NM), and then Sandusky (~132 NM). Assumes good weather and 23-25 knots. Or, you could take your sweet time. NW...
Insurance is roughly broken down into two camps: 1st party and 3rd party. 1st party is when the claim check comes to you, 3rd party of the claim check goes to someone else.
You want to carry insurance if for no other reason than third-party cover....if you hit someone in the water, bounce off...
Sorry this has happened to you.
I have a JetSki, am an insurance geek (broker/agent) professionally, and also have Progressive on my Jetski and autos.
I have sunk my Ski twice in ten years. Once when a bud flipped it (turtled) and he didn't have the common sense to re-flip it back over, and...
So going through the boat and finding things that need to be fixed....replacing a bilge pump (cited above), rewiring a faulty VHF, replacing a battery charger, replacing a bad windlass button on the bow, tracking down a water leak which ended up being the windlass spigot for anchor cleaning...