On my Burb, I tried to get the pan out without raising the engine. No go, that's why I had to lift it. The baffle and windage tray I reference in my earlier post were getting hooked on each other; literally needed a half inch room...that wasn't there till the motor went up a bit. But this was on a 175,000 miles 5.7 that hadn't been maintained well by previous owners. The pan and cooler mount were leaking, so we replaced gaskets and O rings on them. And of course I put everything back together exactly like the GM manual says to, correct torque specs and tightening order...and it still leaked from somewhere under there. More a seepage, but still annoying, after spending all my off days for a month under the truck!
The job had started out as an oil and filter change and replace the belt tensioner. Fired it up after that's done...and orange pee under the truck! No, really, you need a water pump now? And Dad says, let's do the timing job while we're here. And that's when we found out about the plastic timing cover. In 2007, only source we had was the Chevy store, $58 and tax. Now, the aftermarket has them.
But to answer your question,a little more succinctly ( sorry, I get wound up talking about trucks!), try to get to old one off / new one on without dropping the pan first. Then IF it goes in okay, then you know you shouldn't have to mess with dropping the pan. Hope this helps.....