In my experience, there is no wrong time to invest for cash flow. However, the fastest, truest cash-flow plays are with management intensive properties in otherwise undesirable, economically depressed areas.
And since they’re already economically depressed, and undesirable, the major downside risk is some kind of catastrophe happening. That would be something like an earthquake, or perhaps an environmental disaster like the one in California, where the natural gas reservoir was leaking gas into everyone’s homes and causing all sorts of mayhem. Other than that the downside is the level of management required in that niche.
Let me just say, investing in areas where the prevailing culture refuses to assimilate, or you don’t fit that culture, it makes a LOT of sense to find management that resonates with that culture, and you work with the management.
Frankly, this is practically impossible to accomplish, if you’re not willing to set up your own management company and hire the people that understand the culture, and speak it’s language, and understand your goals.
Of course, great cash-flow can be captured over time, simply by paying off the mortgage and regular rent adjustments, without investing in hell-hole projects and neighborhoods. But you sacrifice velocity of cash-flow for appreciation.
As a result, most investors would rather sacrifice cash flow for appreciation, and invest in more bread and butter deals. There’s that, too.
Meanwhile, there’s innumerable ways to capture cash flow, including wholesaling, merchandising, and flipping deals.
I’ve mentioned this guy before, but there’s a cash-flow investor that wholesales deals to come up with the money to buy rentals. He buys one cash-flowing rental for every eight or nine flips he does. Interestingly, he states the purpose of each rental, so that it’s clear to his family what they’re for.
For example, his Flower St. rental pays to feed and care for his horses. The 8th St. rental pays for all the landscape maintenance on his ranch. And another house pays for all his taxes, insurance, and utilities on his personal residence. And the list goes on.
FWIW