@Alan Monahan ,
I have no experience in real estate as of yet but I was alerted of your post via keyword alerts! (Thanks bigger pockets!)
I just wanted to weigh in on your dilemma. From everything I've read and research so far, I am almost certain that the veterans will come here saying something along the lines of plot out your strategy and work backwards. What's your end goal? Where do you want to be 8 years from now? 5 years? 3 years?
I'm big into personal development and the encouragements you hear listening to the podcasts and reading the blogs and e-books heavily, come back to the universal success principals found in personal development: know your why and be committed.
The circumstances and situations are going to be different for every individual, but the success or failure is depending on how much conviction you have in the reason you're going into Real Estate Investing and the commitment to see it through NO MATTER WHAT.
As in all things in the life of business, you're only a loser, if you quit. I hope that this encouraged and helped you make your decision and I would definitely like to keep in touch to add to each others REI network.
All the best,
Dominic