Hagerty Insurance is another option to check out. They offer “agreed upon value” which means you submit photos of the vehicle and an estimate of what you think it’s worth and they either agree or counter offer and let you know the annual premium cost. Along with the insurance coverage they provide free towing, coverage for spare parts and a other services depending on level of membership subscription. I’ve used them for years and had two towing events both with excellent results.
As for paint. I recently completed a top to bottom restoration of a ‘46. Paint and body work was by far the most labor intensive and expensive part of the adventure. Depending on your goal and abilities to do at least some part of the work, the final cost could end up being from the upper four figures to the low five figures. Judging from some of your photos, my guess is a reputable body shop would likely insist on taking the fenders and cab off the chassis and removing all paint to bare metal. Finding a good body shop, in itself is a challenge. There are many threads here in the Stovebolt that discuss this subject at length. It would be advisable to spend some time reading through some of those.
Good luck and as someone suggested previously, it’s best to post specific technical questions in the related forum. So doing will likely result in more views and responses from guys that specialize in the topic.