Congrats on getting through the insurance settlement phase. That is a big step in the right direction.
As someone who could not bear the idea of the insurance company owning my damaged boat which would most likely end up in a dumpster I decided to buy her back for cheap ($800 - $1000 off my settlement check).
The damage to my boat was mostly a hole in the hull deck joint (3" x 12" approx), roller furler, bow pulpit and jib trashed. Beyond that were some sections of damaged teak toe/cap rail.
I had some experience with West System epoxy so I had a rudimentary idea of how that worked. I had never done a more 'complicated' repair that needed a proper camber to match the hull. I could not find ANY fiberglass 'specialists' who would give me the time of day at their mostly $80/hour rates (figured into my repair estimate for Boat US).
I read some books and other websites that detail repair techniques using fiberglass (epoxy + glass): Fiberglass Boat Repair and Restoration
I ended up building a mold for the outside of the hull using a very thin plywood that would bend to match the hull shape (this idea came from a book from the UK). For your repairs you might need molds for both the inside (cabin) and outside. I'm still surprised at how well my repair job has held up and is nearly undetectable. Lots of sanding, dust and nasty thinners are involved with the process, but the better I got at it, the cleaner I could work with less clean up and sanding.
I guess what I am saying is that while I have only seen pictures of the damages to S/V Libby I don't think that those damages are much worse then I was able to fix, myself. I had money left over for other goodies for my beloved boat.
I'm not sure how you came up with your estimates for repair or who you used (if you found people willing to offer an estimate). I still think you should contact Baggett & Sons: Baggett and Sons Marine Restoration
They likely charge a lower rate then most commercial enterprises (read rip-offs) but they might also offer you suggestions on how you might be able to repair your beloved boat for much less then the estimates would have you believe.
If you are sold on the idea of a bigger boat with all of the bells and whistles you are used to then please ignore the above. Just remember that ALL boats need a lot of this or that and the nice thing about the devil you know is that you DO know S/V Libby's positive and negative aspects whereas you will have to start all over with a new to you boat.