I'm a DIY mechanic in training (the internet is teaching me lol). My starter doesn't want to catch the flywheel. I can take a wrench and turn over the motor a few inches and the starter will find a good spot and start the car. How hard would it be for a first timer with basic knowledge to pull my 5.0 motor and replace the flywheel using basic tools (engine hoist, jack stands, etc.)

 

label everything!!!!!!!!!!!!!! wires, hoses, everything!!!! Otherwise its a couple bolts and a lift away. My best advice to you would to be to drop the trans instead. The flywheel/flex plate will still be easily accessible and a lot less work and possible issues in the end. If you have a manual I would highly recommend replacing the throw out bearing, and possibly clutch at the same time. Just to make sure your not doing the work again a few months later.