If you run a short loop of line to the metal handle of the engine, it will give you more leverage in pulling the engine up, and you dont have to lean over the stern so much. I learned this trick on a boat I rented in San Diego once.

I would also make sure the outboard engine bracket and tilt mechanism on the outboard is nicely greased up.

I assume the engine bracket has a good torsion spring to make lifting the engine easier.

As far as tilting the engine goes, maybe a loop of line around the back of the engine might help. Naturally, you dont want any line that could dangle in the water and foul the prop.

I'm just trying to think of the easiest fix first. A Yamaha 9.9 is a great engine. If you go with a smaller outboard, someday you might regret it. No way would I recommend major surgery to cut out an engine well.

West Marine sells a outboard engine tilter that hooks on to the top of the engine cover ($55.00) But, it doesnt look great to me.