A location like beachfront property or a desirable class A neighborhood.

But its in a less than desirable area so the bump in prices isn't going to continue - partially due to the high taxes those areas are seeing. 

I would suggest starting there and then seeing if an online tool is desired.

This chart basically shows me which City's are most desirable (can do the same with Zip Codes):Anything to the right of 0 means the $/sf is growing QoQ on average, and the height is the current $/sf of that market.

As background, it's a 1400 sq ft ranch in a very desirable area where homes typically fetch $500/ft+ after rehab or new build.

The premium they are paying is having the ability to book highly desired dates that far in advance. 

Your desire to travel out of country.You cannot do a 1031 exchange from the US to non-US property. 

Passive income is generally more desired from an investor's point of view because they get a lower tax treatment than active income. 

I have no doubt @Carlo D. will be able to open the bank account he desires but when it comes so submitting loan applications the lender's underwriting team not only has to underwrite the property and review the borrowers PFS and personal information but also has to make sense of the ownership structure and who will be required to guarantee the loan.

That being said, as others noted, if you have the capital and desire to learn, there is very little to do but actually start.