First of all, welcome to e-r.org!
You mention TSP here, so I assume you work for Uncle Sam. My first questions, then, would be:
* How secure is your job (paycheck and health insurance)?
* Does he not have a monthly disability payment? Was the $14,000 settlement in lieu of ongoing disability claims? (Sounds like a potential place for a lawyer.)
* How much do you need to live on (i.e. if you looked at your normal expenses, could you do it with what you earn plus whatever else his sources bring in? (Unemployment will go to zero if he stops looking for work.)
* Even if your job is stable, do you enjoy it enough that you wouldn't grow resentful in having to work another 10-12 years to get all the debt paid off and have enough investment, pension and/or SS income to make it?
* Do you have a pension waiting for you (FERS or CSRS), and how much (and when) would that kick in?
Frankly, a quick glance suggests to me that unless you really enjoy your job and *very* frugal living, I don't think you're there yet. So my gut feeling to your question "is this a pipedream" would be: yes, particularly with your current debt situation.
Specifically, I don't think I'd consider it any earlier than all the debts other than the first mortgage are paid off. Once the TSP loan, 2nd mortgage and credit cards are paid off and your only debt is the first mortgage, AND you've demonstrated that you can live within your means to the point where you don't need to finance your life with more debt, I'd re-evaluate cash flow. But I just don't see the math working with that many debt payments on a $45K salary.
