We would meet once a month and just hold each other accountable for the steps we are all taking in building our RE business. 

But with this being a 5 unit multi-family building most lenders do not offer a loan product that will take the STR revenue into account. 

The best strategy depends on your goals, but here’s a breakdown:Selling outright would result in paying capital gains tax and depreciation recapture, but since the appreciation is minimal, the tax impact may be relatively low.Gifting the property to your son could potentially allow him to sell it with a lower tax rate, but since he hasn't used it as a primary residence, he won’t qualify for the exclusion of capital gains tax on a primary residence, and you'd need to account for gift tax implications.1031 exchange could defer taxes, but you would need to purchase a like-kind property of equal or greater value and meet all the IRS requirements.

I have a US credit score, US bank accounts and some US-based income, but my paychecks are not.

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.

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). 

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).

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.

Sponsor takes personally accountability. 

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