Also, you could also hang out at some local ice rinks where people take their kids to hockey practice!

Practice Pitching: Sellers may not be familiar with subject-to deals.

Reach out anytime agreed. i am unfamiliar with his markets but $220 does seem very low. a sf room mate/ BRRRR strategy seems more practical

I know Deed in Lieu is a common and normal practice.

It comes down entirely to your ability to commit to the deal and close it on time.

Also if you are selling, hopefully your agent has advised you but good practice to have a vacant unit to open the buyer pool to owner-occupied buyers/house hackers.

Nights, weekends, holidays, etc.To keep this on-topic, though...DO figure out what's healthy for you to manage but remember it's a process where every experience teaches you good and bad (and be patient with that process).DON'T sweat the small stuff (damage/costs under $50, undisclosed dogs, etc.) but DO find a way to learn, prevent, put in better practices to maintain your sanity. 

How exactly would Shopify stifle our ability to scale?

My most trusted and often used contractor who lives in the area, and is practically a friend is the emergency contact.   

The ability to see the major issues before you buy is key especially when buying dilapidated early 1900's homes.