I've had my tranny out probably half a dozen times and I think until the last two (which were in the last two months) or three times I've had help. Maybe I can still do it but maybe I'd would hurt myself. Like most things, it's better with a friend.
I don't always remember to do this, but it's a nice idea to put a little grease on the splines of the input shaft to help it go in (staying away from all sorts of comments here!
). I wouldn't say it always makes it but it might and won't make it harder.
I've found that once I get it in the car and generally in place, it takes a lot of shaking, wiggling, cursing, staring, pulling, and pushing to get it engaged with the clutch plate and it's pretty heavy and unwieldly to do all that to it. When you're close, you can pull it to the engine the last 1/2" with the engine to bell housing bolts. Be careful and remind yourself that you're screwing into aluminum so don't use much torque when doing that. If it takes a lot, it probably need some more coaxing.
I use a floor jack to hold it in position. Once it's in a little and is generally supported, sometimes someone underneath it can help coax it. I thought of using an engine hoist but I don't think it would have helped me.
Good luck!