The fact that he is reluctant to deliver it vacant may be a big red flag that the tenants are going to be very hard, if not impossible, to get out.

Not because it's impossible to purchase multiple properties at once (that happens all the time). 

Your commute options from those locations are all good, but all of those areas are tough for deals, but not impossible.

It's pretty near impossible to make a property cash flow positive in SBC without putting a ton of money into it.

The biggest thing I’ve been able to do is network, it’s allowed me to reach capital that is nearly impossible to have at our age.

Looking for an affordable market in CA (seemingly impossible!)

I have a small son that makes traveling to other places for RE difficult but not impossible.  

@Jack NorrisAs mentioned, a lot of times the nature of what you are buying makes it challenging to use conventional loans, but not impossible. 

And, yes I have noticed in my search already that multi-families are near impossible to come across, which is truly unfortunate.

Before we adopted that philosophy being top 10 in our market was so impossibly absurd of an idea, all we did was change literally that 1 thing, militantly being "us", unapologetically, and we skyrocketed.