We live in a great area of the state for wrestling. On any given Saturday or Sunday, there are usually quite a few tournaments from which to choose. You can look on the Pennsylvania Youth Wrestling website to see the tournaments across the entire state: http://www.pywrestling.com/tournaments-events.html
Either is good. Round Robins are great because you are usually guaranteed 3-5 matches for the tournament, win or lose. Double elimination tournaments can also be good as they tend to have a bit more challenging wrestlers attend them.
We will identify a few tournaments during the year where coaches might attend. For many others, there will not be. The best way to handle this is to connect with other parents that are going. In many cases, some of the parents are also coaches and can coach several of the boys during the day.
The coaches will let the wrestlers and parents know, usually at the end of practice, if there is a tournament that they recommend you attend. Some tournaments are for first year wrestlers only, some for novices (1-2 years), and some for more advanced.
This is an individual decision based on your child. Some can handle more than others. Please discuss it with the coaches. They may be able to help you gauge where your child stands.