Additionally if you can live in one unit for a year, then you can get the best of both worlds, better financing and a larger than a single family home. 2-4 is a great place to start, shop around for pricing and see what is available.

She can work at one of the big companies here in town for some experience or set up shop on her own. 

It’s worth shopping around and asking different lenders about their specific jumbo loan programs.Recommendations:Shop around and contact specialty mortgage brokers or credit unions in your area that might have more lenient jumbo loan programs.Ensure you have at least 12 months of reserves ready in case the lender requires it.

again, not shopping on Zillow - but actually walking properties. 

Option 1A: Use the remainder of the HELOC (~$20k) to add some value to the house and hopefully add enough equity to have some left over after paying off the HELOC.Option 2: Find investors to pay off the HELOC for an equity stake in one of the properties.

They don't look at the whole picture when they shop. 

This leads to widespread job losses and closures of schools, shops, and businesses.

Is it customary that they have their process displayed online or in a pricing guide so I can shop around?

This property is close to jobs, shopping malls, hospital and other living infrastructure. 

Suburban sprawl: everyone wants walkable neighborhoods with a coffee shop at the corner, but we have a monoculture of single family homes to the horizon5.)