This is a difficult issue. I know justbroke's take is to simply check the box as contingent/un-liquidated box on the petition. With unsecured debts, this analysis is fairly straightforward. But for secured debts, like a mortgage, not everyone agrees on how 109(e) applies.
The problem, most (not all) districts take the view that debt limits are established by what is contained in the debtor's petition.
contingent / non-contingent
A 2nd mortgage is not a contingent debt. The claim exists against you as of the date of filing regardless of the value. Contingent debts are debts that only come into existence upon some triggering event. For example, if you took advantage of the $8,000 new home buyers credit in 2009, one of the stipulations of that program is you must live in the home for 3 years. If you sell that house before then, you suddenly owe the IRS $8,000. The IRS's claim in contingent, it doesn't actually exist, unless and until you sell the home within that 3 year period.
The unsecured portion of a 2nd mortgage is not contingent on anything, you personally guaranteed the mortgage when you took it out. A mortgage is 2 liabilities in 1, (1) security interest in the real estate, and (2) personal guarantee of the borrower. The house is merely collateral, YOU are making payments, that is YOU fulfilling your promise to repay the debt.
The other line of thought on this is that the unsecured portion of the 2nd mortgage is, in fact contingent, but the bankruptcy is the contingent event. There mere act of filing the case triggers, so the outcome is the same, the debt exists for purposes of 109(e) calculations.
Liquid vs. non-liquid
Liquidity of a claim merely goes to whether the amount is known. Easy example, if the debtor has been sued, and some of the claims include tort or common law claims, the amount of damages that may be awarded is unknown. Thus, the claim holder (the plaintiff) has a non-liquid claim until judgment is entered. They have a claim, but we just don't know the full amount. The key with liquidity is not whether their is a dispute as to the amount or whether there needs to be some minor calculating. (note, in the lawsuit scenario, the claim is not contingent, the event that gave rise to claim, e.g. car accident, occurred prior to the BK, so a lawsuit is typically a non-contingent, but non-liquid claim.)
I think you are in a catch 22 here. Chapter 13 lien strips are all or nothing. And you know the balance of the mortgage. Thus, if you are going to do a lien strip, on your schedule of assets, you must assign a value of the property that is less than the 1st mortgage. What this does, automatically in the petition, is create two entries on your other schedules.
Schedule of Secured Debt. It would show the 2nd mortgage claim, with a value of ZERO.
Schedule of Unsecured Debt, It would show the 2nd mortgage claim, with a value of the full balance owed to the 2nd mortgage.
And keep in mind, 109(e) only says, "owes...non-contingent, liquidated, claims" Note, it does not say "undisputed".
Despite this analysis, you (almost) have nothing to lose by filing the chapter 13, and checking the "disputed, contingent, non-liquid" box. Someone would have to object, the BK Trustee, US Trustee (most likely), and sometimes the Judge will bring their own motion to dismiss.
I know justbroke was able to get around this in his case, so I am sure he will chime in. But the analysis tends to be district specific.
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