This came up as a discussion on buying cashflowing real estate vs. speculating on real estate. This is the one weakness crypto really has, you can't buy any that really cash flows. It either goes up or down in value and that's it. That's one advantage investments like real estate, mineral royalties, intellectual property royalties, etc.... will always have.
I was read questions of people asking when's the right time to buy or is now the right time to buy or when will be the right time to buy..... If you're a speculator, I'm guessing you have to worry about that. I wouldn't know, I'm not a good speculator.
If you're a cashflow investor, there really is no "time to buy" indicator of when you should be buying. Investing for cashflow is individual deal to individual deal. If the deal works, it is time to buy that deal. If it doesn't work, it is never time to buy that deal - doesn't matter what the market's doing.
There are seasons to cashflow. Late spring and summer are great times to buy as you can prep a property for tenants in time for summer moving. Winter yields good purchase numbers, but expect to lose some of that as your house sits empty till spring. I personally love buying at the beginning of March. 80-90% of investors have a job and are focused on April taxes and given that an accepted offer in March could easily close 30 days later, you're only 1-2 months out on spring/early summer movers. This probably isn't as much an issue in the south and I'm guessing your moving months probably avoid the summer heat more than winter cold.
In the end I'm learning more and more as I do this that cashflow REI has much less in common with the general public's perception of stock investing....and has a lot more in common with farming. Every year is a good year to seed. Some years yield more than others. The key to overall success though seems to be seeding the right season for your climate.