@Yosef Itav Congrats on the forward planning! It's great to think down the line. I wanted to echo what @Dan H. said and offer some additional insight.
2020/2021 has been incredible for homeowner's equity, to the sum of a 20%+ gain in value. Definitely not typical and attributable to a number of the markets current drivers (namely, low interest rates) causing bidding wars on every house that hits the market. As the frenzy calms, you can expect two things:
1.Homeowners can rest easy knowing appreciation will still rise 5%+ year over year. There is a fundamental supply shortage that has not been addressed. This past year zoning was actually eased across the county to encourage developers to construct larger multi-unit properties in an effort to meet demand. Again, owners of single family detached homes get the big win. A recent study by porch projects another spike in SD's median home price to the number of 24% which will price it at about $1 million!
2. There is an inevitable increase of interest rates on the horizon. First time home buyers are going to be priced out of affordable housing. The following scenario is based on the purchase of a $600,000 home in SD (below the median home price)
-at 2%: Monthly PITI is roughly $3200
-at 3%: Monthly PITI is roughly $3500
-at 4%: Monthly PITI is roughly $3800
To place that into consumer perspective, a military E-7 (a relatively senior Non-commissioned Officer) receives an allowance of $3225 per month for housing. Anything above that is paid out of pocket. They are in a relatively privaleged position while buying due to the powerful opportunity of the VA loan. But, with nominal increases in interest rates, even they can't afford to buy. The fed expects to begin interest rate hikes as early as Q3 FY22.
All that to say, buying and holding in this market yields massive advantages. Even though, short term, you don't cashflow here and now, it doesn't mean that buy and hold is a bad idea. Markets across the country are in a similar position, where the 2% rule simply doesn't exist as it once did. Even the 1% rule is hard to come buy. In my opinion, if you have the means to buy and hold now, you should. Now, why San Diego over another, cheaper, market? Simply, your gain in appreciation and loan paydown is astronomically different in this market than others. Where, in [insert name here] Indiana, you may gain $100 in equity every month through loan paydown, you get that number in thousands in San Diego. Moreover, as the buyers dwindle due to lower purchasing power, you can expect market rates to increase. Anecdotally, my friend was renting his downtown apartment for $2800/mo. He received orders, and ended his lease. The next month, the PMs had placed the unit for rent for $4000 and received 15 applications the first day.
Although the cashflow isn't immediate, it is a medium-to-long-term guarantee. Through appreciation and loan pay down, the impact to your overall net worth is far more positive in San Diego than in competing, more 'affordable', markets.