Yes.
As long as the crank is at 12:00 (TDC either compression/ignition or overlap) the timing gear can be at 12:00 or 6:00, doesn't matter to the timing chain.
Hmmm...for someone new to this, could be a little muddy. Especially working on a motor already together.
Remember, that chain links the timing of both the crank, and cam together, both timed right. Have to also toss in, depending on the new double roller chain you have, and the two matching gears, the crank gear can have up to 3 timing marks, and slots.
And, since the engine is already together, you have valve spring pressure on the cam. That means, when you pull the old chain off, it 'could' rotate a little.
I'd do one of two ways. One, is, with the old chain still on, rotate the engine until the dots are dot to dot! Crank dot up, cam dot down, in line. Then change the chain, keeping things in place.
Or, pull the chain, then using the bolts for each, the crank, and cam, turn each one into the correct dot to dot. If it's not correct, things will go bad. Just telling you like it is!
Yes, front main seal is bad, and needs to be replaced.