For the 7 years I’ve lived in SF, I’ve pretty much hated on Oakland.

Except for my brief consideration of living in the East Bay my first year out here (desperate to find any job and any living arrangement that would work), I’ve despised going to the East Bay, and have been there like maybe 10 times (airport pickups/dropoffs not included) since moving here.10 times in 7 years to visit a place less than 10 miles away.

Reasons for hating Oakland:

First – when you watch the news in SF, pretty much every night there is footage on some cars burning in an arson fire in oakland. Literally like at least once a night.

Second – ive gotten lost in oakland. there are some hardcore scary areas out there. busted does not begin to describe these areas. In SF, the ‘bad’ part of town is childs play. Its sketchy, and there are druggies and prostitutes and knife fights, but its still like within walking distance of a ritzy area so you have a strange sense of safety

Third – Unlike in Texas, the way it works out here is much like NYC – you hang out in close proximity to where you live. If you live in East Bay, you stay in East Bay (nobody from SF will commute out there and nobody from East Bay will come into the city unless its for work). Knowing this, I haven’t been sold on thinking of Oakland as my home.

Fourth – There are nice areas in Oakland, but these are the million dollar properties, not close to public transportation. There are affordable houses in up-and-coming neighborhoods, but some of those neighborhoods are SKETCHY — like nice house, nice house, nice house, crack house, nice house, crack house, crack house, crack house. Its too mix n match shady.

Fifth — one of the reasons i wanted to move to sf from texas is that i liked the idea of living close to shops, restaurants, bars — having a real neighborhood that you can walk to and do stuff in, not suburban sprawl where you drive everywhere. In SF, this is obviously the case. In Oak –the only places where you can do this are the chi chi areas. Much like many major cities, the downtown in Oak is a barren wasteland after 5pm.

Or so I thought…

NG and I went to Oakland this past weekend to attend the Eat Real Fest–an outdoor festival of street vendors and street carts gathered together in Jack London Square. We took the BART all the way, and walked several blocks to the waterfront. As we walked through the semi-revitalized downtown (not quite fully revitalized, but reminds me of Houston’s attempts–in the same stage– of trying to get living/working/retail back into the downtown), we were kind of taken back. The streets were wide and lined with trees. Interesting restaurants and stores had popped up left and right. Chinatown (this is the real thing, not fakey like SF tourist chinatown) was in close proximity.

Chicken n Waffles, BBQ, Dim Sum, Starbucks…wtf? when did this happen?

We spent the day near th water, and it was *surprisingly* enjoyable. Even in a crowded fest-like atmosphere with frantic, frazzly people, it was actually — not too bad. Compare that to the prior weekend’s similar festival in SF which was miserable — crowded, pretentious, full of hipsters, bogus food, outrageous prices. Both festivals kind of served as microcosims of their respective city and the people who inhabit those cities.

SF — filled with frantic, frazzley dbags all trying to impress one another, all trying to be scenesters, all trying to say they went to this or that so they can be the first to yelp/twitter about it, all scrambling to do the same exact thing regardless of whether that thing/event is good or not.

OAK — more diverse mix of people, affordable food, friendlier people, more organized/more space, relaxed, completely unpretentious, in fact, borderline ‘uncool’, normal.

Upon walking the streets, I said to NG, “It’s like we are in a different city.”  He laughed, “uh, we are?”

Then it kind of clicked — things that had been obvious and overlooked. Maybe the things I hate about SF (cramped and stuffed with annoying people, outrageous cost of living), could be avoided by moving to a new city that wasn’t thousands of miles away (Denver), but one right across the bay. Could this be possible? Can I actually love a city I have disliked – despised even – for so long? Maybe the solution has (to be cliche) always been right in my own backyard.

NG and I have always talked about moving to a loft as our first place. Given that we are young, don’t have children, and both love that minimalistic loft look/feel. In SF, as we were house-hunting, many of the lofts were more expensive than houses, with additional $700/mo HOA fees and limited outdoor space (ideally we’d like a deck or patio).

In Oakland, for literally a third of the price, you can get this:

(also in a historic old factory)

or this


or my favorite one–tho less lofty and more beach house-y

needless to say, where I was opposed to moving to the east bay before (esp okland), the idea has now become very intriguing.

Some things we still have to consider:
– need to live next to BART so we have the option of going into the city easily
– need to figure out commute (more for NG than me — i could take the BART or Ferry)
– is this a neighborhood we will enjoy?
– how sketchy is the neighborhood around the loft?
– places and extremely cheap right now — a 15 yr mortgage is quite a bit less than what we currently pay in rent, even w/HOA fees
– HOA fees — cost of the fees, as well as the (low) occupancy of the bldg potentially driving up the cost of individual HOAs
– Resale value — these lofts were forecasted to sell originally at 2x the amt. The offer prices have been way lower than the listing prices, as sellers are motivated. Is this a result of the economy or inflated/unrealistic expectations during the building phase? In other words, I want a good deal, but I don’t want to never be able to resell the property if needed. I’m not looking to flip the house and make tons of money, i just want a place I can afford that has resale potential in the future.
– Once in Oakland, always in Oakland. I need to know that I can live on the other side of the bay knowing that most likely, I will spend little time in the city

A lot to think about. Add to that the tax break we’d get if we purchased a house by end of year, and things really start to get interesting.

Editor’s note 11/10/15: This was the beginning of the flight to Oakland causing some to call it “The New Brooklyn.” At the time we could have bought something rather cheaply, especially because of the recession. Now these places are probably no longer affordable after years of tech boom/housing bubble etc. Most of my friends no longer live in the city — either they moved to East/South/North Bay or out of the city completely. 

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