Optimal timing for acquiring SFR rental property

[Dave Fagundes]

Here's a paradox I've been thinking about w/r/t buying SFRs as rental properties. The conventional wisdom is that best time to buy is typically late fall/winter; that's when the market is slow, and low demand tends to lead to better deals. The CW is also that renting out properties in these months is very difficult for the same reason; people just aren't looking. So it seems like if you try to buy at the ideal time, you'll necessarily be renting out at the worst time. 

My sense of this is that a deal on a good SFR rental property is still worth going for in the winter. If you get a place onto the rental market, that likely means eating more vacancy costs up front, but those will eventually wash out as you acquire cash flow and appreciation later on. In other words, the longer term upsides of a truly good deal on an SFR rental would be worth the relatively shorter term costs of getting it rented in the off-season. Also seems like you could try to avoid the problem repeating by asking tenants for lease terms that would be slightly longer so they would come due in better seasons for rentals.

What do others think of this issue? Thanks in advance for any thoughts.