OK, this is my favorite topic yet so far :)
I guess I'll start with the goal we (hubby and I) have in mind. Basically we wanted to enjoy life without a day job, yet be able to maintain the lifestyle we love. In our case, it will be traveling as well as wine-and-dining. When we're here however, we don't want to get bored, so the vacation rentals will keep us busy enough. We have hired a property manager to run the SF rentals, so that should be off our plate starting August. SJ is a piece of cake since the the guests are just easier to manage.
As we all know, the challenge was to have enough income to allow us to live this kind of lifestyle. We did quite a few of tweakings in our invesment strategies and figured out a way to make enough between the rentals income and other investment to support this lifestyle. I suspect we'll be doing more tweakings along the way.
Our biggest expenses are really just F&B and airtix when we travel. We are not big into shopping and don't care much about keeping up with the Joneses, so that takes out the pressure.
I really think this is easier and much enjoyable to do because both of us are doing it together. But of course it comes with some risks as well. All the perks that came with being employed will now be fully on us: Health insurance, cellphone bills, even new laptops. But hey, you live only once and who knows for how long, so might as well enjoy it when we're young enough to climb those SF hills!