Right but you then control the appreciation on a much larger asset. In terms of pure net worth and net present value, trading up is a huge gain even if it doesn’t generate more short term liquidity.
You can also rent out the smaller place and get both cash flow and NPV upgrade.
Bro straight up ask your friend to get you laid. Lower your standards and just follow his lead to check that box. Don’t over think it - the goal is to get into a 1 on 1 situation after some drinking (not too much) then just go for it. Don’t worry about it being embarrassing because your goal is not to see the lerson again, its to fuck. Everything will come much easier after that, trust me.
I cannot emphasize the lowered standards thing enough. The sexual context itself is surprisingly stimulating. Even if it goes terribly it will throw a switch in you which just demystifies the process