However, after running the numbers accounting for insurance, PMI, taxes, vacancy, capX, property manager, etc. the property is estimated -1.85% cash on cash return (-$600/mo) once I fully rent the property.

In my experience, the cash flow may be substantially reduced (or even become negative taking into account interest rate of original loan and refi closing costs).

If you do take on new debt or collections during this time, the lender will see and it will require that it be accounted for in your DTI (unless this is a DSCR loan). 

Having "real estate investing" or "real estate" anything, in your LLC name will surely raise red flags for banks, especially as you move beyond net 30 accounts to larger credit lines.

Also, if you have any local Senior Support organizations, they may have a long list of families looking for senior living.  

I have seen it and funded it for others or my own account.

Trusts- Make your bank accounts TOD time of death.  

Sponsor takes personally accountability. 

Hi Account Closed, when talking about multifamily in Calgary, are you referring to duplex, triplex, fourplex or larger commercial multifamily?

Here's what I'm accounting for currently:Mortgage (P&I)InsuranceTaxesElectricWaterTrashInternetVRBO/Airbnb feesGeneral/RepairsCleaning (though these will be passed through)If i'm super conservative on my monthly rate, I will need to rent the unit 10 nights/month to break even, if I am more realistic with the rate (according to my realtor who runs two STRs), i'll need to rent it 7-8 nights/month to do so.