Ridgley, as you pointed out, I am not here to get into a pissing match. Simply want to point out that there are other, way more affordable options out there for small guys. With built in features that match yours, in the end,
First, and, to point out the obvious, I did not imply that YOU charge your customers transaction fees. But I did see some that do, and find the practice abhorrent, sure. Simply preying on unsuspecting small guys who do not know any better.
Second, not going after your or anyone else’s business, I am NOT looking for customers, had my fill of IT by now, just pointing out to others there are different choices in achieving online presence. Especially for those on a shoestring budget until a certain point of growth where service such as yours may become a better choice for some.
Thus… My chiming in, not for first such thread to be clear.
Not sure what double databases you are talking about, we have just one, and it has every customer and sale and related info (sans customer’s credit card info, since I decided to eliminate this option for greater security and privacy of our customers). Even IF we ever get hacked no payment info will be available, and I sleep better at night. Even our payment processor is set up in such a way that actual credit card number is “invisible” to us, just the last 4 digits for tracking, if need be. I certainly do no do any “sync up”. At all.
And since you want to compare apples to apples, and as I am asking for that as well, for days now, I would STILL want to see the $$$$ involved when someone hires you, or some other software house, to run an online store. Our monthly maintenance cost, “tools” and all, is $10 per month, plus credit card fees (unavoidable). Sure, I spend a bit of time per month upgrading plugins, when needed, but it takes all of a click to do that after WordFence sends me an email notice that something needs an upgrade. Up to me, and in many cases I can ignore for a while. Again, pretty much free save for my time to log in and do a few clicks. WordFence also sends me notifications and reports notifying me of all attempts at hacking the site. Yes, many try, as you know 
How much would a winery pay for your services, at the minimum, for “setup and configuration”, and then monthly?
We can talk all we want, but in the end numbers matter. Feel free to disclose the numbers on your end, or this entire discussion is meaningless. Despite the glorified “tools” and “customer retention” you keep mentioning.
As I said already, if a winery decides to go with a software house like yours, sure, its their decision and, of course, there may be reasons for that. Understandable, since we all operate and make decisions differently. But you keep on talking up “customer retention” and whatever other “tools”, when for small wineries that really translates into producing a worthwhile product that keeps customers happy and willing to keep coming back. Sure, customer relations are extremely important, but most small guys do that in any case last time I checked, and no amount of “tools” will improve that. Personal interaction with customers is the way for small guys to grow, and most do that via email and/or phone calls, or winery visits/tastings. And no number of “tools” will retain customers if products do not merit that to begin with, or a winery acts like jerks upon a visit scheduled via your “calendar appointments tool”. And with small guys, customers usually directly email or call for an appointment, again, a personal interaction even prior to a tasting/visit taking place, how would a “calendar tool” improve on that when, in fact, it makes it a less personal interaction, and just an extra step in the process. All for the privilege of paying $$$ for the “tool” than does nothing in the end. All of our customers have access to us, and reach out directly.
I put our numbers on the table, up front. Sure, I coded and spent some of my time, which should really be translated into $$$$. For a one time setup/configuration, so, yes, its a cost. Feel free to use an hourly rate of your choosing, for the 2 weeks of my time, and plug the number in. I haven’t done any consulting work for the past 20 years or so, and have no idea what the hourly rate may be these days for WP+Woo. But, let’s be fair, and add, say, 100 hours on the max on my end, as setup/configure cost.
Again, small guys can easily avoid the effort I invested in, BY CHOICE, and use a free Woo theme and then simply add their products to the shop, add a payment gateway of their choice (free), and let it rip. Not much effort, nor time. Maybe not as “fancy and nice” (to our eyes) as what we ended up with, again by choice, but a solid and workable online presence right out of the box. So, MY cost of setup/configuration is, just as yours, a choice for a winery to make. But, in my case it is this hefty investment is fully avoidable, if a winery starting out doesn’t have the funds to do so from the get go. Is yours?
So, $$$$$ wise, post some numbers. Minimums. Let’s compare apples to apples since you’re doing your best avoiding the discussion so far.
And, actually, feel free to point out any small winery that has more features than we do, even after paying hefty up front and then monthly fees. I bet at least 95% do not. Yes, I haven’t added a mailing/club options yet, but I bet I can add a plugin and be done in a few hours, at worst. So, again, maybe $50-75 plus my time. ONE TIME.