@Mathew Pezon
Sorry for the delay.
Since the two challenges I’ve focused entirely on building a strong and profitable rental portfolio. I’m at the point where the cash flow is strong enough to easily sustain the holding costs of flips, and I feel like I truly know the markets that I would want to flip in.
As far as learning contracting, why not buy a run down rental? It’s just an easy way to learn, and your exit strategy doesn’t rely on a buyer, only a renter, and that’s much easier to put in place. Even if you renovate a little too much, you’re only going to get a better tenant (to a point). I learned half of what I know by working for other investors for free on weekends and days off, and the other half I learned by trial and error and youtube.
I hate quitting too, but leaving one aspect of real estate isn’t quitting the game. There are tons of ways to make money in this business. I’ve seen landlords leave because they hated it and went straight into holding notes – that’s not quitting to me, it’s finding the niche that fits you at the time and builds your wealth.
It’s not about proving myself anymore. I know I can do it, but now I know what I didn’t know before and I have the confidence and knowledge to do it right this time. Worst case situation now is I own a little higher end rental than I'd like.