01Is the $200,000 a fixed fee, a retainer, or a deposit on account of percentage-based fees?
This single question reframes everything. A $200,000 fixed fee is one outcome. A $200,000 retainer against, say, 6% of a JMD $30M estate (= $1.8M total) is a very different one. You cannot evaluate value for money without knowing which it is.
02What percentage of the settled estate, if any, will the firm charge on completion?
Published Jamaican norms are 5–8% for probate plus 1.5–2% for property transfer. If Mrs Madden quotes higher, you have grounds to push back with the comparators. If she says "no percentage, just hourly," that is unusual and worth probing — ask for an estimated total.
03What is the hourly rate, and which fee earners will charge against the matter?
In Jamaica, consultancy is commonly $15k–$50k per hour depending on seniority. Confirm whether junior staff time is billed and at what rate, and whether there is a minimum billing unit (six-minute, fifteen-minute).
04Will the firm provide an itemised invoice for the $200,000 with a narrative of work done?
A reputable Attorney-at-Law in Jamaica should provide this without resistance. Refusal or vague language ("for services rendered") is a red flag. The General Legal Council of Jamaica regulates billing conduct.
05What is the conversation about the rental income from the adjoining apartment?
Rental income arising during estate administration is estate income and must be accounted for to all beneficiaries. The lack of clarity Aunt Lue is reporting is the question — is the rent being collected, by whom, into which account, and is it being declared?
06What disbursements should we expect on top of fees?
Likely items: property valuation report, newspaper notice (two weeks, seven days apart for Letters of Administration), stamp duty ($5k–$25k by estate band), caveat searches, courier fees for overseas documents. These should be billed at cost, not marked up.
07What is the projected total cost and timeline to completion?
A standard, uncontested Jamaican estate takes 10–12 months. Longer timelines accrue more hourly time and more interest on any tax owed. Get the projection in writing so it can be measured against later.
08Will the firm copy you and your brothers into substantive correspondence going forward?
This is the diplomatic version of "we don't want our aunt missing details." Mrs Madden cannot share privileged information without Aunt Lue's consent, but the firm can be copied on operational updates with permission — and if Aunt Lue authorises this in writing, the firm must comply.