patrick.net

why not just buy a place in SF and then sell and buy a place in wine country in 20 years? The appreciation in SF will at least be as good as up in the wine country.

All financial aspects aside, this way you get to enjoy the house you live in for 20 years...or are you saying you get to rent a nicer place than you purchase? and that along with the pain of moving every few years is better?

If I were in your shoes, I would approach the idea differently.

I would take all my money and invest in stock mutual funds. Depending on your risk tolerance, you can choose among "growth" "value" "dividend growth" "index" or "balanced" funds. Balanced fund examples: T.Rowe Price Capital appreciation, Dodge&Cox balanced, Vanguard Wellington.

In 20 years you should have a huge chunk of change to use to buy a place somewhere should you wish to.

Being a landlord has joys and also headaches.

Why subsidize others home for twenty years. They live there and you get to fix all the problems. I think over the course of twenty years you will not come out ahead dollar wise , but will have a house that is paid off if you can keep up with the difference in what you take in as opposed to what you will be paying out.

There is damage, times of un occupancy, and what if they stop paying rent and stay several months till eviction.

A lot to consider. I would just buy when you are ready to own and occupy and save in the meantime.