Pooch,

I do not think it is ever too late to get a dog. They just bring a lot of happiness and companionship to a persons life. If the dog has a good chance that he might out live you, that's OK. Just make sure you have someone that can appreciate the dog is lined up to take it.
Now for the pen raised birds. I am lucky to live in an area where I get some great bird hunting in. Some years better than others. I am also luck to have a hunting partner that raise 15,000 plus Bobwhites and Chukers each year. It is all in the way these birds are raised and cared for. If you raise them in good flight pens you stand a good chance of having some great flying birds. Nothing takes the place of wild birds, but nothing else substitutes for the experience a young dog gets from training on these pen raised birds, along with some pigeons. These young dogs have a great foundation the first time they go out for wild birds. Just like in sports you need to practice before, and even during the season. We normally train with a 20 or a 28 gauge with light loads. I will also admit to have missed a few birds. I would be hard pressed to shoot these birds with a pistol with bird shot.
We have had a great time taking some friends out with us for a shoot on planted pen raised birds, and nothing is much more enjoyable than taking out some young hunters out for the first time, shooting these birds over the dogs. Lots of opportunity for them, they get to see the dogs work, and you can help mentor these kids on safety and with the guns around the dogs and the other hunters.