Yes, flyer is correct. A “fixer” could have been had inside the RSF covenant for well under $300K as late as 1994. However, the cost to “fix it up” under covenant guidelines would have been quite a bit greater than properties outside the covenant, as he can attest to, as there are two layers of bureaucracy to go thru (county and covenant) with the covenant having the final say.
AN, if this is to be your retirement home and you are insistent on the 100′ frontage, I would urge you to consider the many uninc areas of SD Co. You may not get sidewalks but you can’t have everything. As a perk, many uninc areas in the county have a lower tax base than inc areas do, depending on where they are, due to the dearth of services provided (sidewalks, frequent street lights, subsidized trash pickup, etc). A good portion of these uninc residential streets are so lonely that the residents just walk their dogs in the middle of the street and move over when a car is coming.
When you retire, you won’t really CARE about commute time. If you buy the property in the next few years (while you are still working), you can fix it up minimally to lease out and do a major remodel just before or after you finally move into it.
Your problem is that the type of property you want doesn’t usually pencil out very well as a rental, due to their initial cost and carrying costs, incl property taxes.
I don’t think you will be able to find a “coastal” view property in 92106 or 92107 (as flyer mentioned) for =<$800K without either dropping your sf req drastically, buying a two-story, buying on a smaller lot, and/or buying a very heavy fixer. And believe me when I say that the "heavy fixers" of ANY size in these areas are snapped up by VERY local all-cash buyers (neighbors), often as "FSBOs" and "pocket listings." I've been watching (in person) certain pockets of 92106 on and off for over 18 years. And my reqs aren't anywhere near as "stringent" as yours. The best deal, view-wise, I've ever seen a local cash buyer snap up for the <=$300K range was on the corner of Hugo and Clove (Fleetridge) about a decade ago. It was a thrashed two story that termites had taken over situated on a std lot with a fantastic sit-down view of the dtn skyline.
That dude had his porta-potti out and scaffolding and chain link around it within hours of closing and got right to work scraping :=0
And I can’t even tell you how many SD (and SJ!) “boomers” I’ve known who have a seaworthy vessel slipped at Shelter Island. If they could get their hands on a WWII box of ANY size in ANY condition in 92106 for a song, they would downsize from their (Bonita, Esco, EC, Jamul, etc) spread after a gut/remodel and move there in a flash. They don’t mind living in <=1400 sf and neither would I, for that matter :=]
That is your "competition" for 92106/92107.