I bought EQ6 when somebody was selling it for $65. She handled all of the registration transfer paperwork with EQ and had only used one activation. (I got lucky because I didn't know anything about the limit on activations when I bought it.) I wanted to do design, lay out fabrics and colors and get a preview of the quilt before moving forward.
For me it worked. I love new technology but sometimes we buy the latest and greatest and never use those extra features. Consider what you want to do and then make a decision.
At the very least, you could probably resell it if you decide to upgrade. However, you'd have to know how many activations remained for the next purchaser. Another issue might be how many times EQ will transfer the registration. Maybe check on this.