😆 I feel your pain . I also have a champagne taste and a beer budget. And of course you don't have to live where your real estate is. But a duplex and hire someone to rent and take care of it. Doesn't have to be vacation property.

And another option is go in with your friends on a place to live. That one gets tricky of course.

And as one person said , just keep doing what you are doing , but at a higher level. Keep saving investing in stocks. Compounding is very powerful.

When you say "real estate" do you mean to live in or invest in?

If to live in that is tough in high COL areas. To invest in that can be easier because it doesn't have to be where you are.

Example: go in with your friends on a vacation condo to rent and visit. Hire a local RE company to rent and manage it.

I keep them in my 500 lb fireproof safe.

Sorry sir. You belong in r/Wallstreetbets.

Effing complicated. Get a lawyer. For example if you split up , not married, it's a WHOLE LOT more complicated than if you are married. Divorce law is well settled, but not "shacking up" law.

You may say ,"I'll never leave him/ her". But shit happens. IMHO get married first.

No. You can't do any of that. Hire a lawyer. The sooner the better.

Interesting speculation.