Plus, I will have some time to get ready to convert some extra space into another full up bedroom. 

I had to extend the loan once and completed the entire thing in just under 2 years while working full time.

I am an appraiser here in BC but I have found that the AMCs have made it virtually impossible to succeed financially in the field which means it cannot be a full time commitment, namely in BC where I currently live.

I have been looking to manage a sober living or transitional housing building for some time.

I see many big homes available for sale with small price tags. 

I know that most people say to have everything fixed before the closing date, but if it is in writing and signed prior to closing, is it that big of a deal?

.- We could furnish it and go for STR/MTR simultaneously, but we get occupancy near end of October, which isn't the best time for STR.

I strongly suggest you have an attorney draw up the contracts (and one has who has already done this many times, as they will already have templates they use).At the minimum, a lender need a Mortgage but I would also recommend for more protection, a lender will want a JV agreement, promissory, personal guarantee and if possible, to have the deal cross-collateralized with another property. 

@Amby BhagtaniBesides looking at market stats look at the time and energy that you can put into a market.

Jerome Powell announced a few weeks ago that the time has come for the Fed to cut rates, and we are expecting to hear that announcement in the next Fed meeting on September 17-18.