I understand some of the economic factors that can lead one to a particular city or province (or state), but unsure of some of the key elements as you funnel down below that level.Appreciate any insight.Tyler 

Cash offers are often particularly appealing to sellers because they eliminate the uncertainties that come with financing, such as loan approval or appraisal issues.

Boston in particular is a strong market with great appreciation, a great tenant pool, and rents being as insane as they are it's nearly impossible not to pay less when you house hack vs. rent. 

And as someone that grew up in Missouri, this post caught my eye, particularly because I'd never heard of Lebanon, MO so I had to look it up on Google Maps.

Firstly, it often generates higher rental income compared to long-term leases, particularly in desirable locations or during peak seasons.

We also see a lot of ground up projects in HCOL areas that do particularly well. 

An agent told me that 9/10 transactions they handle are cash and not financed - so i think in this particular submarket going in with financing really weakens you.  

As a foreign buyer, you are to look for 2 things in particular: the temporary foreign ban (which they keep pushing further back) and the source - The foreign purchase ban which applies across the board. yes there are exceptions but if you are not a Canadian tax Resident (which it seems you are), you will need to look for communities where the population is less than 100,000 in general. - Another exception to note on that foreign buyer ban is the number of units/doors for your investment: I believe the magic number is 5+ as this would be considered as commercial Real Estate- In Ontario, you will also have to look our for the Non-Resident Speculation Tax (NRST) which imposes about 25% on the purchase tax.

I missed one particular detail from what Scott was discussing.

I furnish and provide amenities that warrants this so I do a lot of work to find comps in this particular space.