Short contest deadlines
Most states give an interested party only a few months after notice to challenge a will. Miss the window for preserving evidence and the fight becomes harder to win on the merits.
Six situations where an executor's paperwork turns into litigation, valuation, or liability, and the specific things a careful reader checks before deciding to hire.

An estate stays clerical until someone else has legal standing to object or sue. That single fact, not the dollar value, is the best predictor of whether you need counsel.
Most states give an interested party only a few months after notice to challenge a will. Miss the window for preserving evidence and the fight becomes harder to win on the merits.
Challenges usually begin with how the will was signed. Confirm the witnesses were disinterested and that a self-proving affidavit is attached before you assume the document is unassailable.
A contestant rarely wants intestacy; they want a prior will revived. Locate any earlier version and read who takes under it, because that tells you what the dispute is really about.
Most of the work of settling an estate is clerical, and it stays clerical for as long as the facts stay simple: one decedent, one will nobody disputes, assets that sit still and can be counted. What changes the character of the job is not the size of the estate but the presence of a second party with a stake and an argument. Once someone can object, or a creditor can sue, or a court in another state has to be persuaded, the executor is no longer filling in forms. A careful reader learns to spot that shift early, because the cheapest time to hire is before a deadline has already passed.
A disinherited child, a second spouse, a caregiver who appeared in the last codicil: any of these makes a contest plausible, and plausible is enough to change how you proceed. Check the will's execution first, since most challenges start there. Who witnessed it, were they disinterested, is there a self-proving affidavit attached, and does the signature date line up with what the medical records show about the decedent's capacity that month. Check whether an earlier will exists and who benefits under it, because the contestant's real goal is usually reviving that document rather than intestacy. Counsel here is not about winning arguments. It is about preserving evidence and meeting the contest deadline, which is short in most states and rarely forgiving.
An insolvent estate is dangerous specifically because the executor can become personally liable for paying the wrong people first. States set a statutory order of priority, and administration costs, funeral expenses, taxes, and secured claims generally sit above the credit card balances and the medical bills. Check the mail for sixty days and total what arrives. Check whether the hospital bill is a real claim or an insurance adjustment not yet posted, and check whether the mortgage is current, since a lender's forbearance ends quickly after a death. If the arithmetic looks close, stop distributing anything. An attorney who has handled a claims docket will tell you which claims to reject in writing, and when.
Real property in a second state usually means ancillary probate in that state's court, with its own filings, its own bond rules, and often its own local counsel requirement. Check the deed itself rather than the tax bill, because a survivorship clause or a transfer-on-death designation may take the parcel out of probate entirely. A business interest or a farm brings a different problem: someone has to establish value, and a number pulled from a bank statement will not hold up. Check the operating agreement for buy-sell terms, check whether an appraisal is required by the will, and remember that the IRS is the authority responsible for federal estate and fiduciary income tax filings, which is where a defensible valuation eventually has to stand.
You cannot close an estate by distributing around a missing person. Courts want diligent search documented, and diligence has a shape: last known address, certified mail returned, a search of death records, contact with the Social Security Administration or the last employer, an heir search firm's report, and sometimes publication by order of the court. Check the will's language for a survivorship clause and a lapse provision, since the answer may be that the share passes elsewhere and the search matters less than you feared. Where the share does stand, an attorney can petition for deposit with the court or the state's unclaimed property division, which discharges you and lets the estate close cleanly.
Serving as fiduciary while inheriting is entirely ordinary, and it becomes a problem only when a beneficiary objects to a specific act: the house sold below the listing price, the car transferred to your son, the fee you took for your own time. Check whether the will authorizes self-dealing, check whether the sale was arm's length and documented with a listing history, and check whether every beneficiary received the same information on the same day. Where objections have already been filed, separate counsel for the estate protects your accounting and gives the court a neutral record to rule on. That record is what usually ends the dispute.
The common thread in all six is that a second person now has standing to be heard, and the estate's paperwork has become the exhibit list in a proceeding. Hire when you spot that, not after the hearing notice arrives.