I think it would be best to drain the trans oil first... on most cars... once you take out the driveshaft and then point the back of the trans down.. it will leak out the rear... maybe it does not on MB's... but it won't leak out for sure if you have drained it.....

Herb... I do not want you to take this as any slight towards my confidance in your abilities... I am sure you can do this.... and I hope without getting hurt... but I would like to mention some things.

Since I am also a Subaru owner, and have swapped engines... I think you are correct to feel that that does not count on this question... after pulling my pushrod 1800 sube engine I picked it up and carried it about 10 feet to get it to the other car.... it weighs less than 200 lbs in that condition... a far cry from your cast iron 5 cyl block with trans attached....

You said you do not have a lift " at home" .. does this mean you are not going to do it at home... or that you will be borrowing a lift to do this ?... Also, your hoist equipment has not been discussed...

It is much nicer to take the engine and trans out together IF YOU CAN REASONABLY DO IT THAT WAY.

However, that entails having the car high enough that you can get under it to loosen the proper items... and then having it low enough that you can take out the engine and trans at a fairly steep angle...

The potential problem comes from several items..Some cherry picker type engine pullers are not designed for the amount of weight At the distance from the cylinder which you need... or if you are using an A Frame, the distance that the chain hoist hangs down below the A Frame plus the engine angle changer (can't think of its name) under the may not allow you to get the engine with the trans still on it completely out of the car...
If you pull it out and need to change the angle as you pull it forward it can get very tricky safety wise....
So, before you commit to doing this with the engine and trans together I hope you will do lots of measureing,,and ask someone with experience to actually look at your facilities .....
If you are going to rent equipment... then consider doing it in two stages... lift and place the car on solid jackstands , then rent a transmission jack and pull the trans...This will greatly decrease the amount of ceiling height which you need to do this swap...