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Originally Posted by Another Reader
For someone that is 40, that would be an excellent idea. For someone that is 65 and has no experience owning and operating properties, that might be daunting. As I get closer to that age, I think about simplifying and streamlining, including reducing the rental portfolio in favor of easy to manage assets. I would not start building a portfolio at my age today. It's too much work, and finding suitable properties in the current market is very difficult.
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Quite right. I passed 65 and do much less of the in the trenches rental stuff now - also think of cutting down on the number of rentals and making life simpler. Problem is the capital gains will cut asset value a bunch, so we would want to try and make 75% of asset dollars produce the income 100% does now. Reality is that rentals have been very good to us (like, we could pretty much sell and stick the proceeds in a mattress and live very well for the next 30 years).
We're not so constituted that we want to just get a check for a set amount every month - guess we like feeling that what we do affects what we get - I like feeling like what I do is valued by others enough for them to pay me. Having Amazon or Facebook shares bounce up or down by 5-10% because someone tweeted makes me feel like stocks are kind of like beanie babies. We do hold shares, because we have enough to do so and I accept that the rest of the world may be correct and I'm a luddite, but they feel ephemeral and the hard money loans and rentals generate the serious cash.
My thought was that the friend may be in a unique position: very familiar with construction and building systems and no stranger to physical maintenance or running a crew, which might translate to riding herd on tenants. He might also have contacts that could point him at good rentals to buy - shoot, maybe he could throw up some new rental buildings for himself?!