You make a lot of good points as to why owning is preferred in the long run but I get it that it is very expensive here if one didn’t buy awhile ago or literally hit the lottery. This would be my strategy if I came here now:
My wife and I would both have to work in order to secure a home here. It is simple as that and probably not that unusual especially for this area. Sure, we don’t have kids so that is one big hurdle we don’t have to deal with or pay for. The fact is, we can probably make a go of it if my wife didn’t work now but since we don’t have kids, what is she going to do all day? Seriously. That dual income just allows us to retire that much sooner and allows us options. Options is what you want.
Focus on a small or fixer home. Hey, we were a family of 7 living in a 3 bedroom home growing up. Too often people also think they are locked in to a property forever. You say, you like to DIY well here you go. I see fixers all the time. I stopped off at one a few months ago in the city when I found out the listing agent was the one who helped me find my primary Sunset residence in a private sale. I had to say hello. Well, the place was a dump but the price was doable and yeah would have required a lot of work. So, what? Don’t think too far ahead and just get into the market as soon as possible. Not only do you stop paying rent but you start getting some tax breaks too. The strategy is to get in, fix up the house, sell it and then move up or get closer to your “dream” house. Since you are married, the first $500k in profit on your primary house would be tax free. I know people who do this continuously and they have kids. They go in, remodel while living there, flip it and bank the profits into a nicer home. If a house is not doable, then find perhaps a townhouse. You probably won’t have as much freedom with it as a SFH but it is a start. You sound like a creative person, so this is where you can put that creativity to good use. I have seen homes that were nothing before but the buyer comes in and does amazing things with the landscape or designed the interior so well that it was literally night and day. That translates to bigger profits when you sell.
Maybe consider a SFH that has inlaw potential, thus, you will have another income stream to help you out with the mortgage. Yes, more money to have to spend but I certainly have benefited from such a strategy.
Save like heck. That means making the short term sacrifices in order to achieve the long term goal. No spending on anything remotely frivolous. No eating out. No cable tv. My grandparents came here with nothing and worked on the fishing piers earning very little and socked it all away to one day buy a place in SF. I didn’t grow up going to private schools or took nice family summer vacations. I have worked pretty much every summer since early teen years. I may not be the smartest person in the room, but no one will outwork me.
Good luck to you!!!