I read you post and I hear you've had an accident, maintenance and structural issues that were big wallet hits, the neighborhood is getting crowded, and life is getting a little busier.
Those are all ongoing issues that, especially that last one, will continue to grow. Life with a 7yo is one thing. Life with a 12yo is another and it can take your life completely over. As it should be but it can leave scant time for other pursuits. Maybe time to downsize a bit. A truck camper would give plenty of space for a weekend and be super easy to handle. Go so far as to consider tent camping. I see more and more of that and they all seem to be having a ball.
At the end of the day only you can decide what works for you and your family. I know you wonder whether it's worth it or not but I wonder if your 7yo wonders that.
Good luck to you whatever the final decision be. Just be sure involve the wife and son in the conversation. Their input may surprise you.