You brought up some very good points that I agree with, and at the risk of sounding like I already made up my mind...
His decision to use cheap, outsourced developers was out of ignorance and not necessarily intentional. Although this decision got him a good handful of well paying customers, it resulted in massive technical debt that he is just now coming to terms with. His core product was customized for each customer with undocumented changes - and almost impossible to roll out new features to without breaking the core product. Setting up a new customer took weeks of developer time. You know, the standard crap that happens when you have a non-technical person running the development team. It became unsupportable.
My efforts over the last year have been focused on converting this product to a supportable, multi-tenant solution with almost immediate setup and deployment (just a couple of hours per customer) - no development effort required.
If we went back 8 months, I would 100% agree with you. The client balked at my estimates. He disagreed with my efforts. He resisted every "burn it to the ground and start over" conversation we had. But in the end, I won those fights and after our successes he now looks to me for those decisions. I have gone from "I can't wait to fire this customer" to "holy crap, this is really working" over the last couple of months.
So yes, in the past, he did not value great people, prioritized cost over quality, and is now paying for it dearly. If the story ended there, I wouldn't have posted.
It's my conversations with existing and potential clients in the industry that got me thinking about this. There are no serious competitors (yet), and as far as I can tell, there is nobody out there working on the solution either. The biggest players in the industry tell us that there's a huge gap that needs filling. It's tough to not get excited about this!
In the interest of motivational transparency, I'd like to share what my plan for 2015 was toward the end of 2014: wrap up projects with most of my clients and focus on building out a couple of my own projects. I have a track record of architecting and building other people's ideas, but not my own.
In thinking through the risks, I believe that working full time on my own projects (with no existing customers, funding, etc, yet) is a bit riskier than buying in to a company that already has paying customers, contacts, etc. I guess what I'm saying is - should I put myself on the line for my own projects, starting from scratch? Or should I put myself on the line for another company that already has some successes and that I'm already a year into? With the latter, I'm not taking on 100% of the risk, and I believe the chances for my own success are much greater due to the fact that I work best in tandem with a business partner.
This post has gotten a lot more personal than I would have expected, but I guess it's good to get it all out.
I do sound like I've made up my mind. I may need to sit on this for a few weeks.
I will definitely post updates in the future as I'm sure there are others who could benefit from my experience through this venture.