:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

This might lighten the weight of the tree toward your property;  so this might help or not. 

I do look to grow beyond two properties, but not necessarily at a rapid pace.Finally, if I were to do this, what are the proper steps in forming an LLC and then transferring them into that entity?

If they indicate they will leave a positive review, the survey will direct them to the proper OTA to leave that positive review.If they indicate they will leave less than a 5-star review, trigger an email to the host/assistant for immediate follow-up.

Housing prices in two of our larger cities (Vancouver and Toronto) are also crazy high (eg $1M to buy a starter home)...actually in Vancouver proper at the moment the cheapest home (single family, not strata) is $1.2M...surprisingly (to me) in Toronto the cheapest home on the market is $650K (ignoring some listed for $1 as clearly there is a catch).Our mortgages work differently than in the US, and what we get for rates are only locked in for 1-5 years (typically) and then we have to renew at whatever the current rates are. 

They should be doing a load calculation, taking into account insulation and window type if I'm recalling how it works properly. 

Screen tenants properly or pay a good PM to do it for you3.

In addition to joining the seller to the buyer at the hip for several years/decades when the seller wants a clean break, the properly-discounted, risk-weighted, money to be received by the seller is less than the immediate sale price.

I also reached out to Proper Insurance, but they informed me that they can't offer their standard policy due to the elevated fire risk at my property.

the reality is you have negative cash flow when properly estimating the expenses on the 3 rentals (no way 3 rentals have $1300/month maintenance/cap ex, pm, vacancy, and misc total (basically $433 per property).