Especially in a big money/high demand area like you're in.

Where will the money come from to be able to do that?" 

We manage a lot of properties in C class areas, there is money to be made, but you need a quality asset,  a great screening system, and you need to be able to realistically quantify the risk. 

When we were looking for property management, we had to read through the fine print on MANY management agreements as they all sounded great when speaking with them, but most actual management contracts were filled with stupid additional charges. 

I am an investor and I also happen to do some private money lending.

Even with my income, most of my money goes to taxes.

Tell the buyer to come up with more money down 

There’s a little too much concern on BP about “piercing the veil” without thinking through just what it actually means.

And ideally sell it 4 years later.If I can more or less count on the renting of additional bedrooms to cover the running costs of the house, I'm really only looking at taking a hit on the buying/selling costs - which SHOULD be lower than what it would cost to house him in dorms for 4 years.I feel like this is pretty obvious and easy (not trying to make significant money here, just thinking I could save $10-$20k on housing costs over 4 years).

HELOCs are variable rates and it's highly likely that they'll actually be LOWER in the near future, why not bet on that?