If he blocks the frame like he says, nothing to worry about-have to get the tires up.
Too bad you dont have someone you trust to run it, that would be best but a pain to put back to bed again after an hour or 2. I used a simple hand transfer pump with an extended hose to drain my tank, kind of rolled one side of the trailer up on a block to get it all to one end.
Have you considered putting it up for sale, 2-3 years is a long time, big chunk of the depreciation is gone already I guess but you may get into something newer for the same money in a few years. It never ceases to amaze me the low hour, quality boats that come up for sale.