If you believe that your product saves money, then you have a chance. If you want to sell at price points like $20,000/year then you had damned well be able to walk in and convince them that they can replace at least one person, probably 2. You also want a pitch where you come to the point very fast - you will be talking to busy people who don't know you from Adam.

But saving money is not as easy as it looks. Take a good accounting system. It intersects the business at a lot of points. This makes it not generic. A few years ago O'Reilly needed to replace theirs. They got a few other publishers to cooperate to create an open source one. I don't know how that went, but I do know it was harder than they expected. Besides, big businesses like having ERP systems be expensive, it is a barrier to entry for potential competitors.

The free rider problem is only partly solvable. You have to convince each participant that their value from participating justifies their work. If nobody can be found for whom that is true, then you have a bigger problem. See The Tragedy of the Commons. And no, annoyware and open source don't really mix.

About buy versus make, the price point will affect this. Also who you deal with. As for best pricing strategies, I don't have relevant experience. Sorry. Nor is this a good place to find that.