If someone is sufficiently motivated, they'll always find ways to crack the software. If you don't have a large "personal" user base (as opposed to firms) - con

If someone is sufficiently motivated, they'll always find ways to crack the software. If you don't have a large "personal" user base (as opposed to firms) - consider introducing a cut-price personal edition to lessen said motivation. Firms using it for "real work" - which I would hazard a guess at your price point form the bulk of revenue - are unlikely in any case to use a cracked or personal edition. Firms in less well-off regions may choose to buy the personal edition and accept the legal risk, but avoid the larger security risk of a cracked version - so you still get some revenue.