How soon did YOU pull cash from investments

[Lee Haenschen]

Working through information overload, cold feet & finding time syndrome here.  An important question me and my wife have been wondering....

So once YOU started buying homes to hold and rent & houses to flip, how soon did you start using the income/cashflow to live off of? 

My wife desperately needs to quit her job to take care of our 2 kids. School has been an issue with my youngest (learning disabilities) She can't quit her job until we replace her yearly income + healthcare (roughly 24K bring home + health) 

That being said, when you started in real estate investing how soon did you start using the income to live off of? I know everyone's situations are different. If you have 5 homes and each cashflows $100 per month after all expenses...did you use that for income? Or did you set that aside in case what you've been allocating for expenses was not enough? Then waited until that account hit a certain $$ value then started taking income after that point? 

The houses I am looking at with the BP calculators look to only have $100-150 cashflow per month (buy & hold) at most. That would take 20+ homes to achieve this for my wife to stay home. Should we be looking into flipping instead for quicker cash? I just worry that we flip a few homes and think that everything is "ok" so she can quit her job, then our ink well dries up! and now she needs to get a job again! My nerves & anxiety has slowed our progress in the real estate market. 

Thanks in advance!