I have two sorts of planes - ARFs that I buy just coz I want to fly them (like, tomorrow!), and kits that I buy because I want to build them. For the kits the actual flight is just proof of my building skills, though these planes rapidly become my favourites.

First up you should be aware that building a kit is ALWAYS going to cost significantly more than buying an ARF, in many cases it can be 2-3 times as much by the time you finish. This is partly due to "economies of scale"... ie: a factory buys glue by the gallon, while you buy it by the ounce... the same goes for wheels, control horns, etc. Also when you're building you tend to be much more "picky" about what you put in the planes... you'll end up wanting those really flashy scale wheels that look just right instead of some cheapie foam ones. Kits almost always have more wood in them and are built stronger, but usually at the cost of weight. Ultimately you'll have the satisfaction of having a plane that no-one else has and knowing it was built right (or that it wasn't and you've hidden your errors!). It also teaches you a lot more about how to repair damaged models than you'll ever want to know. Suddenly repairing that shattered wing isn't impossible, it's an interesting challenge... and fitting flaps to that plane that came without them but really wants them is within your reach. If you want to fly that plane soon though, buy an ARF. I've got a Corsair that's taken me about a year to get to the "almost ready to cover" stage.

As for beginner friendly kits, I started with the Great Planes Perfect Trainer 40 kit. It's really designed as a first build and the instructions give you lots of basic building advice that is missing from more advanced kits where it's assumed you've already got a few builds under your belt. With it's slab sides there's minimal carving & shaping required. The Piper J-3 cubs are also a good starter kit for the same reasons but will let you get into something a little more "scale". They also come in 3 sizes to suit .20, .40, and .60 size engines. If you're feeling a bit more ambitious you could go for a GP RV4, or one of the Goldberg Tigers. I believe the Tigers come with details on how to modify them to be tail-draggers which would make a nice "next step" from your trainer.