So the train I have so far is a Lionel Norfolk Southern in "O Gauge" with the Lionchief control. I read that O-27 will run on regular O, but not the other way around, so I'd rather keep the track at regular O so I can run both. The box mentions "O 36 track", so that's regular O from what I can tell. Am I wrong?
Yep, a 2% grade rises at the rate of 2 units of rise per 100 units of track length. Inches, feet, meters; doesn't matter, as long as rise and run are in the same units.
"O-36" is for a loop diameter of 36 inches, and therefore a track curve radius of 18 inches (all dimensions are to track centerline).
O gauge in the distance between the rails, but different types of equipment are designed to negotiate sharper curves than others. I'm not sure what constitutes standard O gauge equipment, but its recommended minimum radius is 72", per https://www.thesprucecrafts.com/minimum-curve-radius-model-trains-2382285 I model in N scale...
In general you need at least 100 inches to rise 4 inches, (4% grade), but 200 inches to rise 4 inches, (2% grade) would be much better. How big is the table? Basic principles: Keep your arm stretching distance to 2', (how far you have to reach if you need to get at something) Build a frame and put insulation foam shhets on it. Plan on going DCC from the start. As for books? I don't know what is currently available. For now I suggest you keep it simple. Start with putting down: A loop of track A passing track A couple of spurs for industry A two or three track yard. Use sectional track on a foam base. Note: This is over simplyfied. I have never worked in HO or O scales so there are a lot of other factors I'm sure.
Look at this page. It has a nice chart showing the various possible radius offerings: https://www.lionelstore.com/curve