I generally fly freeware, unless there is nothing available and my hand is forced. A classic example was when Air NZ 737-300 flights were my main type of flying. The FFX 737-300 SUCKS... but I had no choice. 50 North came along, and released a B733. I bought it the day it was released. So they are the 'required' purchase by my mind. I loved the 733 flights, but hated the FFX.
Other aircraft I use excellent freeware when they are available. Dreamwings ERJ135 for example. Why get the feelthere when I'm quite happy in the freeware?

Others are just priceless for their quality, and I can't let them pass by. The Level D 767, and the Aeroworx B200 for example.
Others are just too pricey

PSS Triple 777 and PMDG 744
But, freeware is where I started, and we've had it pointed out in this forum numerous times, that there are freeware aircraft out there that are as good as, if not better, than payware (that French Cessna 152 for example). And where else can you find a good Fletcher, or Metroliner?
