Since online review sites are full of biased and inauthentic reviews, are there any personal recommendations for a point of sale + online payment processing and reservation system for a new, tiny nonprofit in the US? About 20 or so local artists will be part of 501(c)(3), which will have scheduled classes, recurring membership fees (for access to studio resources), and retail sales of local artist work (need to track per-artist inventory / commission). Initially they are looking at Square Plus because some of them are already familiar with the hardware, and it seems to meet all the requirements, but a post on payroll processors by @coreysnipes reminded me to look at alternatives. Basic CRM/marketing (probably just bulk email to existing customers about upcoming events) would be needed, but can be separate. The price point of $300 POS hardware and $50/month + <=3% credit card fees looks like an amount that could be budgeted. They are making a Wordpress website, so it could either be integrated with that or just link to another site. Thanks!
@philvuchetich tagging in @ajroach42 as he has extensive experience with Square + Wordpress for such a setup here in Ellijay

@djsundog @philvuchetich square can do everything you've described, but tracking individual artists items is not a built in feature and will require you to set up categories for each artist in the catalog.

This works, I have done it. There is a sales by category report. Items must be in the proper category before the sale in order for report to be correct. (updating the category after a sale does not change existing reporting.)

The square plugin for woocommerce works very well, and handles bidirectional sales sync, inventory management, and reporting. We manage our inventory on our WordPress site, and sync it to square, rather than using square's management tools.

recurring payments, reservations, and email marketing / CRM can be managed from within square, but they are all (reasonably priced, IMO) paid add-ons. I have used all of these features, they work as you would expect them to.

I do not trust square's management/ownership, but I have been satisfied with their product, and it's available integrations.

Most other point of sale systems have fewer/more difficult/more expensive add-ons and integrations, and equally untrustworthy business practices. Square has, to this point, been my lesser evil.

I am happy to answer questions, or provide light consultation on setup. I have done a lot of this.

@ajroach42 @djsundog Thanks! Based on this, it sounds like Square will still be the most reasonable option at this time. Good to know about the "category" requirement - with the anticipated number of artists (probably ~20), it should be reasonable to manage a couple dozen categories. I see that https://www.mountaintowntoys.com has categories, tags, and brands, so that should be plenty of ways to manage items.

I'll talk with the person who is making the website to see what her design and integration plans are - I like how your websites work with woocommerce, and the inventory integration with Square would be really helpful instead of just linking out to Square.

Mountain Town Toys – New, Vintage, and Custom Toys and Collectibles– Free Shipping on orders over $100

@philvuchetich @djsundog we also manage HTTPS://hemlockbazaar.Com from the same square store.
Hemlock Bazaar – A new Appalachian Marketplace