I understand @Tim Spires' concerns about costs to get your site seen, but I think it's possible to do some up front marketing and hire a good SEO manager, and after a few months or a year, you might have enough organic search SEO power that you show up when people search.My concern is in the future and based on no evidence....that said, I wonder whether anyone will be Googling for STRs or VRs in 10 years.

What one should be trying to do with a portfolio is optimize the risk/return given their resources.  

We want to ensure we’re considering potential pitfalls and optimizing our approaches to everything else. 

Get yourself a property manager so that your investment is monitored and optimized.

The optimal time to invest in real estate is always.

BRRR in MF adds tremendous scale as you can drive value through increasing rents and decreasing expenses, resulting in higher NOI (which is really all that matters for MF)3) Any other optimal markets in Ontario to consider for BRRRR'ing multi-family properties?

If anyone is looking to learn a little more about optimizing their financing to buy multiple properties feel free to DM. 

But the kicker that cemented my decision was there wasn’t any optimism from the commercial lenders and that killed my spirit.

This just happened to come up.The point of the story has nothing to do with contracts, optimal strategies to land properties, etc.

The primary difference between these groups of people is their level of optimism.