So I got a free annual copy of my TransUnion credit report and found an unpaid parking ticket that went to collections.

Had studded tires back then, I think I got a warning ticket having them on in the spring, touch of a hassle changing tires for 3/4 months, now we can't have them or chains on dry pavement. :)

The difference would have bought a plane ticket and hotel.

I would see what price to put in a dumb waiter so that at a minimum, groceries would not have to be carried up 3 flights.

Invest in a plane ticket, and spend a few days in Cinti.

Now look up what a round trip flight to ATL costs from the Bay Area, renting a car, hotel room, food, etc.  

Two words...lottery tickets...you're welcome

I considered purchasing a home in the SF Bay area, but some arguments deter me: 1) I am unsure on how long my family will stay in the Bay area – there is a distinct possibility that we will move to a new location within the next 5 years. 2) Houses here are pushing the million dollar mark tying up a lot of capital, which could be used differently (season tickets for the Warriors, anyone?).

Full-time investor, the crowd before said it best, if you are not local simple buy and hold acquisition,simple cash flow, well managed is the golden ticket.

I will focus on the roof, but a similar process can be followed for other big ticket replacements:You should know exactly how old the property is.