I could not believe how reckless that was. 

If he doesn't have it under contract, its likely that he may run a very reckless business, so you need to monitor any transaction with him with great care.

And to do it when price/income ratios are reaching historic highs seems rather reckless.  

I aim for base hits vs home runs a lot of people try for recklessly. 

HOWEVER, telling someone that they can retire next year if they just buy 10 homes scattered across the country (and we've all already addressed the fact that there's no way they actually work in that many markets, they get a referral fee from local providers) is reckless. 

I have been using the property as Airbnb for over a year now and aside from one reckless guest I haven't had any issues with them. 

That doesn't mean to be reckless, but to not let emotions control your strategy, which sounds like what you've done. 

I also feel that we can be content enough that we do not charge ahead recklessly in order to try to obtain all of our desires.

Don't use youth as an excuse to be reckless.

But don't be reckless!!