RE: 2nd plane
If you do a forum search, you will find a lot of information on this subject. Planes like the Sig 4-star, Goldberg Tiger-2, Great Planes Rapture, and Hangar-9 Pulse XT get recommended a lot. Some other options are the World Models Skyraider Mach-2 and Phoenix Models Dolphin.
Your second plane doesn't have to be high wing wing. All of the ones I mentioned are low wing; a step above a trainer but below something like a Cap-232 or 3D plane. Don't even think about a bi-plane yet; they are interesting and fun but sometimes difficult unless you are more experienced.
Hope this helps.