@Nathan Asher Robson
I don’t think anyone can time the real estate market. I’m a newbie but I’d say that your property/investment analysis should factor in market conditions and you mitigate your risk the best you can. Meaning you can find a deal in any market as long as you do your due diligence. I would also say that buy and hold investors (rentals) are impacted less in a down turn than people who flip. Generally speaking your mortgage payments on rentals are fixed and won’t change no matter what the market does. And people who rent from you are just as likely to rent in a downturn.
I have read that historically the overall real estate market goes through 16 year cycles. Things crashed around 2008 so using that metric there’s another 5 years plus or minus before another downturn. How accurate is this? Who knows.
Real estate markets can be very localized so this may not apply in your market. I know that my home lost $60k in value between 2006 and 2008. I recently got an appraisal and it is worth about $5k more than what I bought it for. So if it was over valued in 2006 then maybe at this point the market is where it should be.