Since you mention using a newer motor, it sounds like you have a TBI truck. (EDIT: Doh! Title says '89. I guessed right.) I'd stick with another TBI motor. They're cheap and easy to find, and don't require the modifications that a Vortec motor requires. 454 swap? Yeah, I'd love to do that too. Probably more work than a Vortec swap.
Pull the distributor. Pull your wiring from the motor and remove your fuel lines. Take note where the harness grounds to the front of the block - if you don't bolt that terminal onto the new motor, it won't start. It took me a week to figure that out the first time I did it.
I use a HF flat ratcheting wrench to take the top transmission bolts loose. For the lower bolts on each side I have a three-foot extension and an impact wobble socket. Easy peasy, good and greasy.
With a TBI motor, you drop the torque converter cover, remove the torque converter bolts - a flexplate holder is worth the money, and your transmission is free.
(EDIT: Disregard!) With a Vortec, remove the support arms to the motor mounts, unbolt the torque converter cover plate, and remove the torque converter bolts. It's another degree of difficulty over the TBI motors. Thin wrenches and strong fingers help.
Your hood will be in the way. I usually wrench by myself, so I take a thick old comforter and lay it across the windshield. Tie a rope onto the hood latch and tie it to the back bumper. Unbolt one side of the hood and let it rest on the comforter. Unbolt the other side. Pull the bottom of the comforter up to cover the hinges. Pull the hood back with the rope until the hood's laying out of your way.
Take the center bolt loose from each motor mount. Raise the engine just enough for the top half of the mount to clear the bottom half. Wiggle the motor, and if it starts separating, coax it with a prybar. DO NOT PRY THE ENGINE LOOSE. You're only using the prybar to wiggle it and convince it to separate from the transmission. If it doesn't come free, check to see what's hanging up. I've never had to get violent with a prybar to get an engine loose. Sometimes you might need to put a 2x4 on a jack and give the transmission a lift.
Once the engine is free, start raising it, checking every foot or so to make sure nothing's attached. I've been wrenching for a couple decades, and I still find stuff attached most times.
If your hoist won't get the engine over the core support, you can pull the core support or take the front wheels off and lower the truck down. My Stepside cleared. On my Suburban I lowered the front end onto the shortest jackstands I had, putting the brake rotors about an inch off the ground.