Over the last few months we have listened to/read countless podcasts and articles to gain a better understanding of real estate investing as a whole.  

Rather I'd prefer to hold property and gain from it on a monthly basis.I know it's more complicated from that, which is why I want to learn.So basically, I'd like to know if you have any specific material for off-country investment, vacation property that may only work half the year (In Crete, I understand the island is not active during the winter), management, and biographies/success stories/mistake stories of such cases.I type as I think, so I might be all over the place, apologies for that.Thank you very much!

It is surprising what you can gain by watching people.

While the property may not still return 20% cash on cash, it would not be losing money on a monthly cash flow basis (hopefully..)But I think that is lazy and irresponsible, especially if you own anything more than a property or two.So I generally try to run what if scenarios on each property and then subsequently run what ifs on my larger portfolio to make sure that the portfolio can weather any economic storm that may come through.I have only been in RE for a few years and didn't gain the experience from 2008 so my question to the group is what scenarios do you test or have you encountered? 

Your example is basically like living off capital gains by selling stocks until you have no stock.I'm looking for something that pays me dividends but increases in value over time, adjusted for inflation.... 

I would then live on the second property for the two years as to avoid paying taxes on the gain.  

I've been in a country where nobody can own real estate.But the best of all was Turks and Caicos, where there is no income tax, no capital gains tax, no real estate tax and no inheritance or estate taxes, if that doesn't encourage real estate investing, I don't know what will.

@Joe C  Thank you for the insight.  

If you gain advantage by letting an agent double-end a deal, then that agent is not being ethical.

The Novice Investors has a lot to gain if the Experienced Investors sees the effort.