The new build will have lower maintenance costs in the near term, but that will eventually catch up you with you.

But the point of dating is *usually* to find a spouse and eventually you have to commit. 

Less risk.Surround yourself with a good team: Get advice from others – a good real estate agent or property manager can make things way easier.Have a plan: Know why you’re doing this, whether it’s to rent out or eventually sell.Just start: You’ve got the research – now it’s time to take action.

The most likely scenario is that his renters will eventually do something that costs him a significant loss, despite cutting them a major break for so long. 

Because, based on prior experience, we all know that eventually the card will come up where that stock is now selling for $50, and you'll make a KILLING.

I then bought a duplex and eventually got bigger.

Eventually 1031 and defer until you die.

Eventually, we did get tired of being landlords, and as our children came along and started growing up, we stopped doing it.

But if so, you don't have to convert your LLC to an S-corp (or create one) in December.

Most hit all the bullet points excepting:Spending $175 on renovation and adding square footage or unit count does NOT miraculously convert to valuation.