In core functionality, it's a game of pros and cons. Dear's POS is pretty good now and it is clearly a focus for Dear so it is seeing a good rate of development. A year ago I personally would have been much more cautious than now. But I still haven't seen it in use anywhere really busy.
Already it has some features that Vend can''t match, such as management of stock transfers and (soon) using a retail store to fulfil orders taken on another channel, such as Shopify.
Vend has an add-on ecosystem though, so people extend Vend to get good loyalty schemes etc, which Dear can't match very well (potentially). You should make an inventory of any add-ons in use and then you will have to decide. Also, you should make sure your printer(s) and scanner(s) work, etc.
Thanks, Tim. Much appreciated. We don't use any add ons in Vend so that's not an issue for us. We use it simply as a front end for Dear. Hardware is certainly something to bear in mind although I see that Dear have broadened it out a bit recently. Thanks again.
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