I'm a software developer (mostly web development) and maybe my thoughts would help you make a decision. My initial response is that the software in general wouldn't be complicated, but a lot of possible complications would make me hesitate to consider the project if you approached me.
Generally speaking, software guys are *scared* of hardware. So thoughts of having to setup a card reader doesn't make me want to jump on this project.
Also, point-of-sale systems are notorious for being poorly done. Unfortunately, they also seem to be very expensive so people are not very willing to have them replaced. If your loyalty card needs to be integrated with a point-of-sale system, I'd almost immediately reject the project.
So, the main *scary* parts of this project are:
1) Hardware - Is the budget of the project going to be worth the headache of dealing with hardware?
2) POS - Is there some trash system I'm going to have to fight with that is impossible to work with?
1) Find a programmer that has some experience doing restaurant type of work.
2) Be willing to pay a good amount for custom software.
3) Check out Square (https://squareup.com) and Square's Card Case (https://squareup.com/cardcase). You may be able to use them or have a developer write some software to integrate with their app.
4) Make your own cards and then manually scan them (i.e. just type in the card info so the programmer doesn't have to setup a card reader).
Let me know if you have any questions. Good luck.
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