This is a very rough comparison, for Maui island only, but in 2012 median condo price was $356,158.

Which island are you buying on?

I know that the general guidance is that emergency funds aren't to be invested, but given our financial security and the fact that we already have a personal e-fund in a safe, non-volatile location, would it still be crazy/unwise to invest this 15k in an S&P500 index fund in a brokerage? 

Is this strategy something I could deploy in a high entry area like New York/Long Island? 

I used to live in the lower mainland but invested where the numbers work like Vancouver Island or Northern BC.

When choosing a location for your first rental, it’s great that you’re considering factors like crime rate, population growth, employment rate, and price-to-rent ratio—those are all key metrics.

happy to talk but your location may  be different then where I used to do student rental.

What works best really depends on your goals and risk tolerance, but here’s a quick rundown of what I’ve seen happening in the area:STRs: These are still solid in vacation-heavy areas like Naples, Fort Myers, and the barrier islands.

For example, in the New York area, especially in some hyped-up fringe neighborhoods (like certain areas of the Bronx, Queens, or Staten Island), finding a "bargain" seems easy.

Deals are location and market specific.2.