The van we moved was 21 feet deep on the sand putting the top at about 14 feet. We filled our inner tubes using 200 feet of hose run to a compressor on shore. Even though we floated the roof of the van to the surface none of the tubes popped, probably because the tubes themselves only rose about 14 feet and we hadn’t fill them completely to begin with. We had to use rope tying the tubes together so they didn't escape through the front window and back where the doors were no longer there. I would think a boat might be easier since you only have the companionway opening to deal with. I have 32 years of diving experience in all types of situations. Black water, caves, wrecks, etc. but even still, if it were me I’d hire it out. Even if the boat isn’t worth a large amount you’re stuck at this point. It is easy to get hurt or dead on something that appears to be so simple.
Our little prank took all day to pull off. It would have been much easier if the previous owner had left the keys in it.
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"I cannot not sail" - E. B. White