It comes down to how much time you save using the software. If software A costs $100 but takes 20 hours to do the same thing that B (costing $1000) can do in 2,

It comes down to how much time you save using the software. If software A costs $100 but takes 20 hours to do the same thing that B (costing $1000) can do in 2, then it's a no brainer. It's a interesting price point, because for my work, $1000 is expensive, but reasonable if it's necessary software. $5k isn't an option unless it can provide serious value, and above that is pie in the sky. (Until they work for a company, most people don't value their labour). Typically $1000 doesn't get you fantastic support, you might get a year of email/phone, but don't expect much. A one off payment of $1000 is nothing compared to some SaaS's that advertise hundreds of dollars a month for premium tiers, or tens/hundreds of dollars per user per month.