You just have to have the right mentality and the develop the skills over time. 

He will occupy it, but doesn't qualify for conventional mortgage. 

I am qualified for conventional financing, but think sub 2 has the following advantages in this case1.

You'll only get to prorate the the gain between the time you lived in it (qualified use and tax free) and the time it was investment (non-qualified use and taxable).2.

Just find a qualified condo in a building that has a decent amount of units and send a couple rounds of mailers to the owners.

It allows you to start EXTREMELY simple and free, while adding tools to your skill-set, without having to recreate or alter your data.

So yes, your ongoing cash flow will be less once you borrow more, but, the reasons you'd be buying that second property are: it's undervalued; and/or it has potential for you to value-add using your specialist skills; and/or even when you refinance all your deposit back, it'll still be paid off by the tenants, with no further regular payments from you.

I'm trying to qualify for a HELOC.

I'm trying to qualify for a HELOC.

For example, let's say that you have a building that qualifies for a Fannie/Freddie except for occupancy.