I think there tends to be a general misconception that wine in general is a good investment . As @Brocklehurstj says it simply isn’t true unless you’re dealing with very high end, limited production and sought after bottlings.
If you intend then to invest in your drinking future and then decide to sell on at a later point of the wines you own then ensure you either keep them in bond and/or stored offsite with a reputable merchant. It’s difficult to resell wine without proving it has been stored properly .

What’s the smartest way to invest in wine so the hobby can pay for itself one day, or is that an unrealistic expectation? Am I being reckless in my spending?
There is a long-standing piece of advice about investing in wine. it goes like this…
'if you want to make a small fortune in wine investment, start with a larger one! (freely given)

it simply isn’t true unless you’re dealing with very high end, limited production and sought after bottlings.
This is actually a relief. I don’t need to factor this in and can just buy wine I know I’ll enjoy drinking. Thank you.

if you want to make a small fortune in wine investment, start with a larger one!
Someone gave my this same advice about opening a restaurant!
Yup! it’s pretty universal for many dodgy schemes. Caveat Emptor!

it simply isn’t true unless you’re dealing with very high end, limited production and sought after bottlings.
I will add to that impeccable and traceable provenance.
I love Au Bon Climat Pinot Noir. Also enjoyed the PNs from Oregon - what do you think of them?