It will really depend on the lake levels, the ramp angle and the tongue on the boat trailer. Your generator does appear to be at the back and that far back the risk of submersion is something to take serious consideration. The other challenge is retrieval, as you know. From what I see, it's going to be very risky and I'm not sure I'd do it.
I launch with our Winnebago and I've seen a lot of different setups over the years try, and some fail to launch. One time we were camping and guy had a very nice Diesel pusher and nice boat, he never launched the boat himself. In the bay of his rig he had maybe a dozen, or more, cases of beer. He'd go find a guy with a pick up he said and make a deal. His boat never spent the night in the water. Smart man if you ask me.
One option, I wouldn't do it to tow with it, but for launching might be to get a tow bar extension to put on/off.
