SF Saga: A Diamond in the Rough (part 2)
This is the second of a six-part series on my San Francisco Real Estate Saga, a months-long period involving countless house tours, sleepless nights, gut-wrenching decisions, and a total of three separate moves. The goal is to give people a sense of what’s involved with buying real estate, no matter the location or price. In the first installment, we heard how I ended up San Francisco real estate market. Now, I’ll talk about finding the perfect place…or is it?
With our San Francisco lenses squarely in place, we saw a series of properties and applied a discerning eye to each. Here were our search parameters:
- Price range of $400 – $500K
- FHA loan-eligible: at the time, FHA loans were the only real option, which meant any place we’d buy would need to meet the FHA’s guidelines
- Condo: no TICs, or Tenancies in Common, which are difficult to sell and require large down payments
- No slick condo developments, unless they had mega character and charm
- Sunshine! We were not willing to live in SF’s famous fog, meaning we’d only look at properties on the east side of San Francisco, where the hills keep the fog at bay
- Walkable neighborhood: we didn’t have a car and didn’t plan on getting one
- Rentable: we wanted to ensure we could rent the place either furnished or unfurnished, in case we didn’t want to sell by the time we were ready to move
For the first couple weeks, we were optimistic. Each place we saw was nice but each fell short of our expectations in a different way.

It looked like a dream--in the photos--but once inside, you could practically touch all four walls standing in place.
To wit, here are just a few of the places we toured:
- Adorable Victorian in a great location. Nicely updated and a liveable layout (rare for old Victorians!). Detraction: common areas were run-down, indicating the HOA was lax and not on top of repairs.
- Stunningly remodeled cottage tucked away behind a row of quintessential SF Victorians. No expense had been spared–every square inch of space was practically gilded. Crown molding, dramatic fireplace, high-end fixtures–this place had everything! Expect one key thing: it was the size of a shoebox. LIke, I literally might’ve had a hard time fitting both our bodies and a pair of shoes into this space. We were used to NYC living, to be sure, but weren’t ready to throw down hundreds of thousands of dollars for a tiny hotel room.
- High-end new condo development. Fancy finishes, high-end appliances, a doorman, roofdeck, and gym in the building. Detraction: the condo had windows on only one side, making it feel like we’d be living in a box. Plus, the neighborhood had zero charm. Next!
- High-end new condo development, with a split-level layout, making it feel much less like a box. Tons of amenities in the building, and an overall good vibe. Central location, within walking distance to several great neighborhoods. Problem: the immediate vicinity was a no-man’s land. It was clear residents drove into the garage, and never left the building on foot.
- Adorable bungalow perched on a big hill in one of SF’s most desirable neighborhoods. Stunning view of the city. Updated finishes. Detraction: Huge, huge, hill. Our realtor’s Escalade barely made it up the hill, so I wasn’t optimistic about my legs’ chances, especially carrying a load of groceries. Goodbye, view!
And on it went, with our hopes piqued, then dashed, over and over. Since we were looking as a couple, the emotional ups and downs were magnified by two. Adding to the stress was the fact that we were eager to move out of the temporary living situation we were in at my family’s home. Right around week three is when you, as a buyer, start doubting your standards. Maybe you’re asking for too much? It’s not fun to feel so disillusioned.
Then we found it. A place that made us feel at home. A place that took our breath away. A place whose detractions even seemed reasonable.
It was in a historical building that had recently been converted into condos, but retained many of the historical elements. Tall ceilings, an industrial vibe, stunning views of the vibrant streets of San Francisco. Perhaps best of all, it was right in the middle of downtown–we felt like we were in a real city, something that we’d felt was lacking in many of San Francisco’s sleepy neighborhoods. The city vibe melted our cold, New York hearts.
What’s more, the price was at the low end of our range, the developer was very eager to sell all the units, and the building was already FHA approved. We felt encouraged for the first time in our search.
The big negative with the condo was it was located right on the border between San Francisco’s tony touristy downtown and the most blighted neighborhood in the city. Like, we had to step over sleeping (we hope) homeless people each time we’d come view the condo. One block to the west, we’d be in front of upscale boutiques. One block east, and the only thing for sale was a rock of crack.
But we were tough New Yorkers, right? We could handle the clash of worlds until gentrification expanded to the blighted area. We had specific reason for hope–a fancy shopping center had just been approved for development right across the street, with plans to open in 2 years. The upside to our investment seemed tangible.
By now it was Thanksgiving week, and the night before we were scheduled to fly home to see family, we met our realtor to write up our offer.
Read the full story:
- Part 1: Mad Dash Real Estate Hunt
- Part 2: A Diamond in the Rough
- Part 3: Making an Aggressive Offer
- Part 4: Back in My Arms Again, But Do We Want It?
- Part 5: Perfection Discovered



At RSRE, we know how intimidating it can be to even consider buying a home, and we hope to help demystify the process, give helpful unbiased advice, and inspire you along the way. [
