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Since inheritance planning is already on your radar, include the proposed ownership arrangement in the first meeting rather than treating it as a later estate question. Ask how sole, joint, or other available ownership structures would affect registration, succession, and administration if an...

Agreed—the electrical and plumbing investigations should happen before flooring, paint and fitted kitchen work are released. I’d keep the higher preliminary contingency until those findings, moisture investigations and approval responsibilities are documented. After that, reduce it only if the...

What falls under “moderate energy upgrades”? Lighting changes, controls, cooling equipment and improvements to the building envelope can involve very different trades and lead times. I’d define the intended outcome and included systems before tendering. Otherwise bidders may allow for completely...

Is the multifamily one property under your control, or several units inside a shared building? That changes the comparison considerably. Also, will the coastal home be rented or occupied by you? Vacancy and management workload matter far more if both options are investments, whereas energy use...

The caveat on rejected offers is that they are only useful if you record why each one failed. Price, terms, timing, and seller preference are different signals. Otherwise it is easy to conclude that every rejection means “offer more.” I’d also keep a small category for unexpected fees rather...