We would then brainstorm for ideas to help them overcome  those. 

Your being young and having the drive might help your mom to overcome this hardship. 

But you have the "chicken and egg" problem to overcome first: how do you prove you're a "closer" when you can't get the time of day?

It makes a buyer's job harder to have to overcome these unrealistic appraisals.

is there any advantage to leveraging debt as opposed to just paying outright im not aware of (my husband is very risk adverse)?

I do not see the purpose of only allowing close in bookings i.e. 3 months except maybe you can capitalize more on events that have not yet been announced or scheduled, however that can be overcome with dynamic pricing software.

This is another case where education can overcome "fear of the unknown".As for mortgage acceleration, it's really too big a topic to try and fit into a forum post, but here's the "short version":HELOCs aren't borrowed against mortgages, they're borrowed against equity (the value of the property over and above the balance owing on the amortized mortgage loan).

I'm negotiating one now but it involves educating everyone, including the listing agent, and overcoming people's reluctance to move away from a regular sale.

It's an old stigma that when overcome creates opportunity.  

At the same time though- I don’t want to adversely affect my family by getting in too much of a rut.