"I can't justify paying someone labor, because it will cost more to pay them than what our holding costs are. So that math equation didn't work out. At what point did you decide to scale up?"
-Our last project was a BRRRR, where my brother and I did a substantial amount of the labor on a very intensive rehab/restoration. I hired two outside contractors to help us. You probably want to test the waters by bringing on a contractor to do 1 or 2 specific tasks. We get quotes for painting and, given the amount of time that it would require, it made sense to hire someone else to paint the entire interior and exterior. It would not have been worth our time. We also hired a contractor to install tile flooring and a new concrete entrance. For me it came down to evaluating the time to do the job vs the bids from a couple of contractors.
I think you should start small in order to get some experience working with contractors, getting bids, and weighing whether to do a job in-house or sub out.
Your specific project is unique, so only you can compare those options and determine the best way to go.
In general, people grossly over-hype 'flipping' and make it seem so easy to do. It is easy to show a before and after photo, and ignore all the analysis, estimating, bidding and management that is required. It is hard work to identify a property that will be profitable as a flip. And if you are lucky to have an operation in place, and a consistent ability to source leads, then you will be far more competitive than a beginner or part-timer who has little to no experience in either, and difficulty finding contractors willing to take small jobs with someone they don't know.