Hi @Victoria S.
Just wanted to add a little bit - the $250k is only the tax free portion. Holding for the last 15 years in the Bay Area has yielded more like ~triple valuation, so depending upon starting number, could be a lot, lot more appreciation to access with mortgage or HELOC. Buy/Lend with Heloc, refi to standalone mortgage, rinse repeat. The next 15 years is your guess but IMHO likely to be less as we are peakish now and 15 years ago was a relative dip... could still be dandy.
I view cash flow <--> capital appreciation; risk <--> reward; investment <-->speculation as spectrums not digital values, and any specific property lies somewhere on those spectrums. It is up to the purchaser to accurately estimate the position, make the risk reward decision or be pleasantly surprised or hit with catastrophe :-(
Anecdotally, one can "force" appreciation on single family on primary in the Bay Area: locate nearly the worst house in the nearly the best school district; renovate, add sq foot; add bedrooms, bathroom; add in-law etc etc. This usually does not raise tax basis (land) at anywhere near the same percentage as potential rent/sale value. Scrape and rebuild has also worked over the last few years too.
IMHO multi-family lies lower on the risk scale as higher rent/appreciation ratio ie higher percentage of your return is in your hand (but taxable). And especially wonderful if you can force the initial chunk of $x00k appreciation , refi, rinse repeat: Love the @J. Martin primary 4-plex route, if you want the cash now rather than wait for tax-free appreciation upon death. Clearly @Arlen Chou and @Amit M. SF reposition multis, and Professor extraordinaire: @Account Closed have the best of both worlds cash now/quick reposition then continued high cashflow + Bay Area appreciation. Not everyone has the skill/intelligence to do this :-(
One thing I conservatively consider when aiming for Bay Area appreciation is to envisage the worst case(s) that I want to mitigate (loss of job, withdrawal of HELOC, earthquake, high % vacancy, high % drop in rent) and answer the question, how can I ensure that I do not have to sell low.
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