Well....you need to use the New Math Of Shelter. The days of having guaranteed income off selling a house are long gone. Over the last 10 or so years I've always counseled people to make the financial part of their housing choice by comparing total costs of the alternatives. For most people that results in renting, not owning their shelter. That is a big difference from the old days when we were raised.

By the time you factor in all the maintenance you cite you may be able to go to a nice rental and be money ahead.

The other part of the calculation in non-monetary and is how much you value one particular life style over another. Some folks just prefer certain styles of living and are willing to pay for it. If that is you then just do it.

Oh yes, climbing the ladder: If you hire someone be sure you cover your liability bases. Wouldn't want the neighborhood handyman falling and then living off you for the rest of his life, now would we?