This is a wise path to follow as long as one has job. But what is the best thing to do when one reaches retirement age, or say age 60, and still has a mortgage?
Hypothetically, let’s consider an example of someone who has $4M accumulated in savings, and owns a house in RBA valued at $4M, but still has $1M in mortgage balance at age 60. Should such a person or couple sell and leave the Bay Area?
IMO, If one has to relocate for retirement, one should do so before actual retirement so that there is enough time to grow roots in the new community.
For a place like SFO that is not really car friendly, look for good access to Public Transportation. SoMa may look like place that will be close to Caltrain/BART etc.
This is about individual financial freedom, concept under personal finance. There are lot of if and else depending on individual savings, future planning etc. Take an excel and do all planning and calculations.
Simple Answer: You need to be completely free from all loans/mortgages by retirement and have reserve cash for rest of your life(you & spouse) !
There are ways to handle:
BTW: I stopped giving all such advices/postings, except easy ones from my memory, nowadays due to lack of time !
The retirees on the Bogleheads forum seem to be overwhelmingly holding onto their mortgages because they are low interest rate (< 3%). Their argument is that their portfolios are making 5-7% per annum, even when conservatively invested in 60/40 stock/bonds, whereas they are paying 2.5-3% interest on their mortgages. So, they recommend deliberately paying just the minimum required monthly payments on mortgages and using thd interest rate differential to make good money
I guess it comes down to how much more in assets does one have at retirement, compared to mortgage. Maybe $1M mortgage balance at low interest rate is fine to carry into retirement if one has built up a $5-6M stock/bond portfolio….
How much you need for retirement depends on how much you spend. Unless you plan on spending more than 100K a year after retirement you don’t need $5M.
My grandmother had a place in Tampa. Probably a little more happening now. If you are retired you can live anywhere. How about Hawaii?
How old are your kids? If they’re “kids”, I would look Noe / Glen Park / Cole Valley etc. If they’re in 20-30s, all of what @manch mentioned are great. South Beach (or East Cut) is a prime neighborhood where you can jog along Embarcadero, walk to 2nd st restaurants / Union square, and ball games. We still look back and that was the best yrs we spent in BA.
Dogpatch still isnt fully gentrified, but getting there (note: you do get some odd people from Bay View but increasingly rare).
Renting out is tricky in SF. In cheaper neighborhoods, you get odd tenants and rent control / renters rights will play against you. In pricey neighborhood, you’d be lucky if rent covers your mortgage, let alone taxes / hoas. That’s why we sold, and we still maintain near the highest price point in the building (and that was 3 yrs ago).
Our friends just started renting in south beach neighborhood: 20+th floor, awesome Bay/City view, full amenities, 2b2b. Rent was around 5k; Given the sales price is around 1.5M, prop tax + HOA + parking would cost 3000+. The owner would be juuuust covering PITI minus the principal. 
@manch, you keep mentioning THs in south beach, but I’ve yet to seen any THs in that area. Do you have any examples? Perhaps we’re not speaking the same lingo.
I meant TH’s in general, not in any particular area. I once toyed with the idea of buying a TH rental years ago in dog patch or SoMa. So I knew they exist in those areas. Don’t know about south beach.
@notabene, Thanks for the detailed response. Kids are in the 20-30 age range. After the Miami tower collapse, I am a bit scared of the big buildings. I think townhomes are probably safer going forward.
What is the latest of Leaning Tower of San Francisco?
The city should take it over and make it a homeless shelter.
I liked this idea as a joke but why waste taxpayers money on a waste building to benefit the private investors?
But how many of the people who are negotiating remote work are actually moving to remote places.
I think many of the people working remotely are staying out in the communities of their choice. I see that RBA towns like Cupertino, Sunnyvale and Mtn View are fully populated - all SFHs, THs and apartments are fully occupied. These have not become ghost towns. People are not moving from Cupertino to Montana. They are just staying in Cupertino and working remotely from their home on most days instead of going to the office from 9-6 every day
The few who left for places like Austin are driving their RE prices to record high. I am very curious how sustainable this trend will be. No doubt many want to have their cake and eat it too.
The rule of thumb is that if 100 K per year is required to live in retirement days and assuming one lives for 30 years in retirement, then approx 100 K * 30 = 3 M is required, assuming no other source of income like SS or inheritance, or income from real estate.