I supervised the construction about two dozen new homes for Habitat for Humanity. Most were vinyl sided, all were done by volunteers. Somehow they all ended up looking pretty good when we were done. Your idea is good, but there has to be at least one person who knows what they are doing, is willing to patiently teach others, and is in charge enough to make the call, when things don't look too good, and a do-over is required. Vinyl is both easy and deceptively difficult. Any monkey can nail it up, and it will look like it. There are a lot of things to know about the hidden details, loose nailing, expansion of the material, leaving gaps, etc....The great part about vinyl is that you can make a mistake, gently take it apart and start again. The vinyl siding institute installation manual is a free download, and an excellent teaching tool. One trick that I use with volunteers is control lines. I snap a chalk line below the windows and above the windows and doors, all around the house. The lines are dead straight, and can be used to gauge your progress, and keep courses even. Once you are cutting short sections between windows, you partially drive a big nail into the line on each side of each opening, then hook your measuring tape on the nail and measure down to the short pieces of siding. This keeps everything straight and even as you side around openings. Good luck.