RE: First Plane
If you're going to fly a .40 size high wing trainer with a flat bottomed wing and some dihedral, with tricycle gear (my recommendation) you will need a large, remotely located field. (for adequate room.) I suggest you find a club that flies from one, and ask about their training program (if any) and whether a club member might have a retired trainer, cheap. You can get help, a place to fly, and possibly good equipment at a reasonable price.
If you insist on having a plane before you go to a field, I suggest the Sig LT-40, the RCM Trainer 40, or the AeroStar. There are others that are fine, those are my recommendations. Good engines for your purposes would include the OS and Tower .46 size offerings, the Thunder Tiger .46 size, Magnum .46 size, and others.
I also recommend an instructor, and if you have the money for a flight simulator, I claim that is also a good investment. Results may vary.
Good luck,
Dave Olson