Think outside the "box" Pun intended.  

I am wondering rather than buying a house if I should buy a rental property outside of San Francisco and live in my currently rent controlled unit until my wife and I absolutely have to move out.

I ended up putting down 10% on a 2 bed condo in South Boston and using my excess cash to buy a cash-flowing asset outside of the city with a 25% down commercial loan.

You will attract better tenents and your property  value will appreciate. everything will cashflow depending on how much money you use as your down payment, however using only 20%, you will need to look outside the Gta Try looking at Peterborough,  London, Kingston or Brantford. 

This was done by any of the following; a statement showing the down payment transferred “outside of closing”, funds transferred to the title company as a down payment but actually from the seller, the seller “purchasing” another asset from the buyer for a heavily inflated price, the reported price being in excess of the “real price” with the seller taking a “silent” second, and something known as “disappearing” earnest money, “paid” directly to the buyers attorney.

The obvious path is just to collect the last month's payment outside of Zillow for the outgoing tenant.Appreciate your inputs on this.

I live in this multi-family so I take care of the grass/lawn, snow removal in the winter, etc - however, I plan on moving out this year so I'm in the middle of deciding whether to hire someone to take care of the outside work or include it into the lease for the tenants.For the lease agreement, I used the old one the previous owners had and made small changes but there's nothing specific to snow removal, lawn care, or other general household maintenance (changing light bulbs, air filters, etc.) 

The triplex were living in right now we bought as a Duplex 2 months ago because the bottom two units are currently connected (and only one of those two units have a kitchen) and the top unit you have to go outside and up the stairs to get to.

To your point, contacting agents outside the area code is a smart move.

I am looking at other markets outside Texas.