The line about Word having too many features is that everyone uses 10% of the features... the problem is that everyone uses a slightly different 10% of the features.
One thing you should try hard not to do is look at the competition and write it off as crap. It's highly unlikely that your antecedents set out to make a shit product. It's likely that when they were starting out, they wanted to create something efficient and streamlined, but then years of paying customer feedback took things to where they are today. The folks at 37signals always used to remind us that it's much easier to add a feature than it is to remove one.
I wonder how much of the shopkeepers reactions were fighting change vs just not trusting someone who didn't come from where they came from. There's real class anxiety around the blue collars vs the 20-something software millionaire set (which is likely how they saw you, as the other, even if you're actually their neighbour). I wonder what would happened differently if it was the owner of the first shop leading the pitch. I often advise founders that they shouldn't get into any business where one of the founders doesn't have deep industry experience and connections. If nobody on your team has ever managed a hotel, it's highly likely that you will fail to disrupt hotel management. Anyhow, it's unclear from your writing but seems like your first customer guy was just that - a customer. In other words, he found someone to spend a month doing free fan service for an idea that if he was truly that excited about it, he would have hired you or at least proposed a partnership and been much more aggressively involved in doing the initial customer development conversations with you.
I'm intrigued by the notion that they have no problem installing their own servers. This pretty much lines up with a certain segment of blue collar and [what I'd describe as Meyers-Briggs 'S'-type professions]... heck, I've seen those computers. They are always covered in a slick of oil and dust particulate. I wonder if they would have been comfortable with an on-site solution that is also connected to a central service, like Github Enterprise. In this way, they have working infrastructure even if you decide to ditch software for comedy, and you can both push new updates and offer remote backup (which is good for risk mitigation) as a paid extra service.
Do sheet metal shops have a trade magazine? Is there an annual sheet metal trade show in Vegas? You might still find it interesting to attend.
Note that of course you're not passionate about sheet metal. The entire premise is ridiculous because even the sheet metal people see it as a job. The whole point of doing something unsexy is that in some ways it's hard because not everyone is willing to do it. I would change and do some things differently, like getting that first customer to put a lot more time and money on the line to explore the concept in a partnership capacity, but if you want to follow the FreshBooks trajectory you have to start with a fractional subset of functionality targeting a micro-demographic and THEN grow into the Intuit competitor over the next decade or so. There was never going to be an overnight success and you'll probably need someone to put in some adventure capital so that you don't burn out after a single month of customer development.
While it's true that you failed to come to the table with a solution to a hair-on-fire problem the other sheet metal shops were having, try to remember that they have good reason for conservative skepticism about something that could turn their business upside down. A lot of this stuff is just an expression of the lowest levels of Maslow's Hierarchy. Everyone wants to be the hero of their tribe, but nobody wants to be humiliated in front of their tribe. The only way to sell into those shops would be for your first customer to make the leap, and then have someone else that already agrees with that customer make the leap and show everyone else that it's safe.
https://www.youtube.com/watch?v=V74AxCqOTvg
It's not the first customer that is the most important. It's the second one! Also: flying doesn't kill you, landing does.
In the end, his comments about how someday they might need the extra features is probably most telling. Deep down, people are scared of the future and they make a lot of irrational decisions based on things they've already done but also on things that they imagine they will do in a perfect future. People will double down on purchases that they've already made so they don't have to confront the quality of their first decision. And people will buy books on Amazon that they don't have time to read because in an imaginary aspirational future, they have an opportunity to real all of the books, and that person will be so smart and awesome compared to themselves today. A huge amount of purchasing in North America is aspirational. Kitchen appliances much?
Onto the comedy app! Bandsintown/Songkick for Comedy is a really great concept. I agree that scraping is a fools errand. However, it's also really important that you replace scraping not with your time but with someone you hire from the internet. Not only is your time way too valuable, it's not a realistic test of what will be necessary to scale it even a little bit. I definitely think that you should find some comics willing to pay even a token amount to use your service to host a reasonably nice homepage for them. You might find it useful to watch this presentation by the founder of Bandcamp at #XOXO. https://www.youtube.com/watch?v=MaUkS-lr-ZM
I do have a small beef: you say that you were making an MVP. What could possibly justify using Vue or any SPA to build something this simple? When did it become the default to start an MVP using tools that are designed to solve Facebook scale problems? I know that it's not just you and I'm probably farting in the wind, but this topic gets under my skin because the day absolutely will come where people look back on the SPAs-for-everything fad and profess that "not everyone was doing it, just the people who didn't realize they were conforming to the pack and reinventing simpler tech that already worked better than it ever had in the past". Your filtering needs were pre-solved by Isotope, for example. https://isotope.metafizzy.co/