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For capital gains, request two worked future-sale scenarios rather than a vague answer: one assuming a sale after a short holding period and another after the intended holding period. Ask what purchase costs and later expenditure should be documented, how residency at the time of sale matters...

We can replace several systems with one platform, but that risks losing specialist features. Keeping the current tools avoids that disruption, yet staff are already re-entering details and chasing the latest file. I’m trying to work out which choice creates the harder problem to undo. Has...