When I do buy conventionally now I put at least 20% down on 15 yr terms because I hate    PMI and 15yr rates are lower.As you start amassing paid off rentals you’ll see how little a few hundred or thousand per month in ‘extra cashflow’ you get by stretching out your til death multiple decades really matters.

Farmer bought it for less than 50k  decades ago he is now rich right.. 

In my case, I met mine a decade ago and I continue to make her money. 

Even if it does generate income at some point, there may not be enough left after debt service to support you.Student loans are the predatory lending of this decade and the ones before.

Since my current risk tolerance is quite high, I’m wondering if I should invest in real estate only after a few decades when I’m close to retirement and have lower risk tolerance.

I have only been in real estate for one decade but I’ve seen things change drastically with technology.I am sure self managing will develop even further to a point where it will become the norm.

And I'm sure you're aware that dividends have been declining every year for well over a decade.

The refi til ya die (trademark) strategy is slow and steady, and has enabled us to pick up houses over the last decade. 

@Ali Boone and Account Closed are two actual investors who have purchased properties and have been investing passively for the better part of a decade or longer.  

I have a property that has a humongous deck that was built decades ago.