And someone jumping into this as a complete newbie can expect that they have a decent chance of making some expensive newbie mistakes.

When you go inside, you're verifying that the condition and estimated rehab costs match your expectations.

How much time / cash / other are each individual expected to contribute?

Our experience has been that MTR residents do not book way in advance of their travel and they want to see great pictures, so being pro-active won't be as big a deal as you might expect.

If the marginal cost increase in buying a house that can be house hacked (a house with a basement, a duplex, etc.) is less than the rents you expect to bring in from renting the additional space, why not do it?

While there are some markets I feel are so saturated it is near impossible to be successful in todays market (Orlando), in most competitive markets you can be successful if a) have reasonable expectations and b) do everything right (price, location, pro design, pro photos, etc etc). 

Nobody on here is likely interested in investing in a small village in Southern Spain as it would make no sense but there are loads of Americans investing in the Costa del Sol so it's important to focus on what matters to the community if we want to help and make sure we don't discourage them with involuntarily misleading statement.In comparison, Southern Italy has none of that, expect for the little Amalfi Coast at a very small scale.

Do you need an S-Corp depends on your overall tax situation and profit you are expecting form this flip.This post does not create a CPA-Client relationship.

I can't imagine being in a partnership with someone that brings nothing to the table but expects the same return as you do.

In the long term  expect RE to appreciate at a rate equal or greater than CPI.