How can you make money in this environment?

[Paul Sweetman]

I've been an investor for 30 years. I own and manage 60+ units. Best life ever. I've always said I'm an investor not a speculator. Properties are being priced at levels I don't understand and if I bought them they would sit empty because my rental market couldn't afford the rent I'd have to charge. BUT these over priced properties are flying off the market in 4 to 5 days. I'd like to think I know what I'm doing but I will not buy a property and not have positive cash flow immediately or at least know what I have to do to get to positive cash flow quickly.  Can somebody explain to me what I'm missing? Depreciation and appreciation are great but I can't pay a mortgage payment or water bill with it.

[Joe Splitrock]

I have learned that my experience can work against me. You see the market as it is today and as it was the last 30 years. Someone starting out sees the market as it is today and as it will be for the next 30 years. Two different perspectives, but looking back creates limiting beliefs. Looking forward has risk, but given enough time and the right market, it is almost impossible to fail.

I remember scratching my head back in 2016 saying the exact same thing that you are saying. Looking back at those deals, any one of them would have been an amazing investment. At some point I had to accept the reality that others see value where I don't. That can be even tougher when you are experienced, because you are admitting that someone with less experience may have a better view of the future.