RE: learning on Sim.
Unless you are going to fly in a large field near your house... I would still have a instructor stand there with you and a buddy box cable. You may feel comfortable flying on your own, but that's $400 that could end in one mistake. The instructor can sit there and let you fly. When he feels things are in danger he can take over.
When I qualified I was perfectly fine letting someone jack in. Yeah I've flown for several years in the past. This was a new field and people that are unfamiliar with my background. Although the person I qualified with said he was fine with me on my own... I left that decision up to the qualified trainer of the club.