As a few other said, as long as the cylinder is cracked loose, it should allow air in there and should be easy to lift. If you don't crack the bolt/head screw loose you will be fighting vacuum/back pressure (not sure if that's the right term) but you know what I mean.
I'd place a 2x4 under the engine resting on the yoke/block and let it down so it stays.
Myself I use a M-Y Wedge that slips (securely sleeves) over the tilt cylinder bars and you lower the motor back down onto the rubber pad. Nice shock absorption unlike the typical yoke up and off the trailer which has zero shock absorption and hammers every bump of the trailer onto your engine. Also take exactly 3 second to put on a 3 seconds to remove instead of crawling around under the boat.
https://m-ywedge.com/