There's a property in Cascais I've been looking at. Here's where the math gets uncomfortable.

I've been looking at the same property in Cascais for a while now.

Not casually.

I've run the numbers more than once. I've rebuilt the spreadsheet from scratch just to make sure I wasn't accidentally proving what I wanted to believe. I've looked at the floor plan enough that I could probably sketch it from memory. I've spent evenings walking the neighborhood on Google Street View, turning corners, checking what's within a five-minute walk, seeing what everyday life might actually feel like.

And every time I finish, I end up in the same place.

The math works.

Which is exactly what's making me uncomfortable.

When a decision gets this expensive, "the numbers work" isn't always the end of the evaluation. Sometimes it's the beginning of a different set of questions.

Am I missing something?

Have I normalized a risk because I've looked at this property too many times?

Or is this simply what making a six-figure decision is supposed to feel like?

Those are very different problems.

Over the next week, I'm going to evaluate this property publicly.

Not to convince anyone it's a good investment, but to see whether the conclusion still holds up after every assumption gets challenged.

And I'd like your help.

If you've bought property before, invested overseas, or you simply think I'm overlooking something obvious, tell me.

If this were your money, what's the first thing you'd try to prove wrong before making an offer?

— Joe