I can't comment directly on the WWS5 software. I'm in the POS business, we develop our own POS software used by a particular hair salon franchise, we have helped various small businesses with their systems, and I've done a lot of research on other POS software programs.
Excluding Microsoft and Intuit (Quickbooks) who have jumped into the POS business in the last few years, most POS software companies are small by comparison. To hear stories of various bugs and update problems is not surprising. They just don't have a big enough installed base, and enough technically minded customers to fully debug their programs. Microsoft has more beta testers than the entire installed base of most POS companies.
While the number of years that Windward has been in business is encouraging, your best evaluation criteria is the quality of their technical support. If they help you with the updates and patch the bugs quickly, and most importantly explain things clearly, that is a good sign. There are literally hundreds of POS programs on the market, so don't be pushed into anything.
