Bryan, you know your situation better than anyone, but don't you think you should be generating enough income to replace your salary before you leave your job?
That's my benchmark anyway. I haven't even started but I have some experience from about 10 years ago. Once I get some things done on my own place and purchase my wife another vehicle, I'll be ready to invest. I have some cash, so that should help me secure some property. My plan is to flip one, measure results, then adjust. Long term I want to buy and hold property, but it seems most people take an uncomfortable amount of debt on to secure these properties. I dont' want to assume that kind of risk. However I will do more research on the topic and assess when I get there.
In 2008 I did a flip with a REO property, bought for 25k, put 35k into it, rented for 800/mo, sold a year after for 85k. It was one of the most profitable projects I did as a builder percentage wise. I should have stuck with it, but I took a job out of state and haven't done any rei since.
If I can manage to do that a few times, I can purchase a buy and hold outright. Then I'd be more comfortable taking on additional debt given that the one property would be paid for.