If the closest house or other structure you could damage is 300 yards away, you might be fine for normal flying. The problem will be if anything goes wrong and your plane gets away from you, then you might be endangering some one else. I fly my nitro planes in some public areas including a soccer field where the closest house is a couple hundred yards away, but I keep these houses behind me at all times, and the area in front (to the East and North) where I do most flying has nothing but corn fields for 1/2 a mile. If I were completely surrounded by houses 300 yards away, I'd stick with foamies.

As far as tuning the engine, this is where you really need some experienced help. Yes you can learn on your own, if you have the budget to pay for your mistakes, but it will be cheaper to get some help to learn how to tune the engine and make sure everything is set up properly. Glow engines can die at any time for a variety of reasons. When cutting the throttle for landing, they will die if they are not tuned properly or the linkages and servos are not set up correctly. You may also have the same bad habit that I did from flying electrics. I was in a habbit of sliding my throttle trim all the way back before landing so that the propeler would completely stop. This is not a bad thing with electrics especially if you want to practice dead stick landings, which you should! A glow engine should be set up the same way so when you want the engine to die you just pull the both throttle and trim back. Problem with a glow engine is you can't re-start it in mid air like an electric. When I started flying glow engines, it took me a few deadstick landings before I got it thru my head to leave the throttle trim set so the engine could idle.

As far as landing, you need a lot more room for approach than you do with a foamie,especially while you are learning. When you first started flying that T-28 you probably needed 100 feet of paved runway and at least 200 feet of approach to get it down. If you are very experienced with it now, you can probably set it down in 50 feet of runway with 100 feet or less of approach. I can land my T-28 in 25 feet of pavement if I need to and have a good approach.
Same thing goes with nitro planes, now that I am experienced with my Avistar, I can land it in 50 feet of paved runway if I've got at least 200 feet of approach. But when I first started flying the Avistar I probably used 200 feet of runway(grass) and 300 feet of approach. If you've got this kind of room and some experienced help, you should be fine.

As far as repairs, balsa can be more expensive and time consuming to repair than foam. Wish I could sugar coat it, but with foam you can usually throw some glue and tape on it and be flying in a few hours or less. Balsa is not really much more difficult, just takes more time and a few more accessories are needed when dealing with the wood, glue, covering, etc.

Hope this helps, keep us posted