As someone who doesn't spend a lot of time in that part of the city I just consider that part of North Park TBH. The whole area from Hillcrest, University Heights, North/South Park and Normal Heights would all be pretty cool to live in. South toward Golden Hill, Logan Heights and Barrio Logan is cool too but more gritty.
Winter here is awesome. 65-70 near the beach every day. Perfect weather for riding/hiking. All of our local riding is prime right now especially after a bit of rain. The desert areas like Palm Springs and Anza Borrego have similar high temps in winter. Our mountains get a bit cold but are still rideable unless we get a dump of snow. Late spring until October temps can be very hot unless you can get up to elevation or be near the water. You can still ride, but mostly early morning or sunset or you'll bake.
There are homeless here but you don't really see the disgusting, massive permanent camps right along freeways like you see in Portland, Seattle or LA. It's an issue, but I wouldn't say it affects livability here.
Inland.... wouldn't say it gets you anything except a bit of a different vibe compared to the beach communities. Areas like North/South Park more urban feel. Others like Poway or Rancho Bernardo are more suburban. Those areas might a bit cheaper, and definitely hotter. During May gray/June gloom there isn't a lot of sunshine at the beach. As soon as you cross I-5, you're probably out of the gloom.
MTB is pretty spread out here, but many areas can be connected together pretty well. This loop is from my old place. From OB add 5 miles of bike path each way. So not really MTB from OB, but I'll take it.
https://ridewithgps.com/trips/109396334. Stagecoach 400 route:
https://ridewithgps.com/routes/29589301. Local MTB club puts on a ride each year to connect a bunch of trail networks together. This is that route, plus the ride home to OB for 60+ miles:
https://ridewithgps.com/trips/109396432
Not a climber, but there is lots of good climbing as I understand. Check out
https://www.alliedclimbers.org/
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