I'll sit anywhere but Terrace Reserved. Some of the Terrace Reserved seats are ok if you know exactly what you are getting, but I would prefer to always be in front of the steel poles. Terrace Box are good for an affordable option, and I still think Upper Deck Box gives the best view in the ballpark.
I'm coming from a fair distance south of the city, so I typically have to drive. Taking the Metra to the Red Line is usually more trouble than it is worth, especially when it comes to getting home at night after a game. For night and weekend games, I usually take advantage of the Cubs remote parking service at 3900 N. Rockwell St. They have buses running back and forth starting 2 hours before the game up until I think an hour after to shuttle people back and forth from the lot to the dropoff point. For other games, I used to park on the street just north of Irving Park and west of Southport, but there were some changes made to the parking rules this year that make LV2 parking a riskier proposition since street parking is only allowed until 5pm regardless of what time the game took place. That means if you park on the street and a game runs a little long, you are at risk of being in violation of the parking rules and ticketed/towed. With that said, I have started using SpotHero more, but I'm still in search of a better (preferably free) parking option, even if that means a bit more walking.
The food is fine for what it is, but certainly isn't the best ballpark food around. Always get the grilled onions on the hot dogs, and stock up on the free dill pickle spears! One thing I have discovered more recently is that the giant soft pretzel in a box is worth the extra money over a regular-sized pretzel. Those standard soft pretzels are almost always terrible anytime I get them and taste like they are multipel days old. I think a regular pretzel is about $8 and the giant pretzel is close to $20, but the giant pretzel will feed 3-4 people and is almost always fresh. I have started just buying the giant pretzel anytime I take my son and we will just eat off that for multiple innings. Also, for the beer-drinking traditionalists, there are still a few places where you can buy Old Style, which is still my go-to beer whenever I'm at Wrigley.
I haven't ventured out much in recent years and can't remember the last time I went south of Addison. Whenever I get something to eat or meet up with friends before or after a game, it is usually at Yak-zies. My wife enjoys Big Star, so we will occasionally go there as well, but I can't speak to much outside of that. The Diner Grill off Irving Park Rd. is another great spot for breakfast or late-night food further away from the ballpark.