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Good points made above. Here's my take on it.

Firstly, I reckon it depends on where your propertry is and what the property market in that area does. For example, the property market in Auckland is growing at an almost alarming rate, has done so for over 10 years now and the real estate gurus say it is likely to continue. As Minnewaska said, at some point you're going to want to go home and if you have sold your property in this kind of market, there is no way you're going to get back in unless you have some serious cash reserves which is unlikely.

Secondly keeping a property works a whole lot better if the property is paid for (mortgage-free). Then you have positive cash flow that can take care of the maintenance and even damage rehabilitation. It will also cover the cost of insurance and a management company to look after the property and the tenants. If the property is properly maintained by the landlord, tenants are less likely to damage it. And it means that if a tenant bolts, you're not placed into immediately negative cash flow caused by mortgage payments.

In our original cruising plan we agreed that real estate had no place in a crusiers life but that was when we had a mortgage. When we go, we will be mortgage free and consequently our view has changed.

If you are servicing a mortgage, none of the above works and you're probably going to regret having the property. :(
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