Having some room for error is key when starting out.

She has blocked my number and hasn't returned her keys, I can't get a confirmation from her stating that she moved.

The key idea that seems to need clarification in this thread is this idea of "brokering" without a license.

Handyperson is the key.

What is the key ingredient to consistent deal flow and getting them closed no matter the climate of the market?

You can still charge a fee for this, because you then have go over there to put the key back and change the combination.

The key is to find a comfortable balance of each. 

The key whether they are worth one dollar or 1 billion is what is their motivation with the property and how can you craft an offer that creates a WIN-WIN to get to a yes where both parties meet their goals?     

The key difference between the two is that IRR requires modeling an exit, and for inexperienced investors, that one major assumption, years in the future, has an outsized impact on IRR, which is less than ideal.

While I do think that there are a lot of reasons to remain cautious and underwrite as if there will be an adverse cycle during the life of any asset acquired today, I think the long bull run in income property has a lot of runway left in a lot of geographical areas.Your family is smart to save some dry powder to take advantage of opportunities, but I suspect that if they are waiting for a reset of pricing and an opportunity to buy at a discount to today's pricing they'll be waiting a while.A key difference between you and your dad is you have a lot more time to make your money back if you get into the market and subsequently get wiped out.