You could jump in your boat and be in the ocean after a short ride?

I have been doing very suboptimally (e.g. taking a large stake in money market instead of riding on the stock bull run).

If you had the opportunity to buy a building for $850,000 at 50% down versus putting the same amount of money into the stock market and just letting it ride (assume VTSAX as the vehicle) which would you choose?

Very popular and we get quite a few groups who come just to ride the trail.They all bring their quality bikes.

When I moved here 15 years ago all my co-workers had snowmobiles and were riding every weekend.

It's a fun ride.  

You could even buy properties out riding cash with that much dry powder.

This has been a wild ride and I'm only getting started.Do you have any words of encouragement I could share with my mum/family?

I don't think you're doing anything wrong; it's just a hard ride to Disney or Universal.

In that scenario, if that happens, the prices will go up so they want to buy now and ride the wave.Like you I'm not buying, but this is fundamentally why the "Greater fool theory" exists.