My personal advice:
1. The three worthwhile investments are to get a good knife and a good sauce pan and frying pan. Others may follow, but I think those three are fundamental. Cooking school equipment is just fine (Even though I have better knives, I still routinely use a 20 year old Mercer Millennia set that I got for the culinary electives at University as it's very high quality for what I do and the chef's knife is around $20 today).
2. Unless you're obsessed with a specific ingredient (rice for us), getting versatility out of your appliances is better than having one-use (exceptions for food you eat all the time like rice or bread where it may be worthwhile). Modern pressure cookers make many recipes idiot-proof. They also are inexpensive nowadays.
3. Eat out what you cannot realistically cook. Things made at quantities like soups, duck, or large barbeque might very well always be better than you can cook due to economies of scale. Extremely complicated or subtle food like Regional Italian (Sicilian and Lazio/Roman), Polish rustic, or Xi'an cuisine are examples where the production is complicated enough that casual cooking isn't really an option.
(If you think you can make outstanding Italian cuisine without major practice, I suggest you go to a decent Italian restaurant to disabuse you of that. In the Philadelphia/NJ area, Zeppoli near Camden and Aldo Lamberti's is a lesson in humility with the same ingredients).
4. If your area supports a Whole Foods (Paycheck), there's definitely better organic stores in your area. If you are in the Pac 12 (except Utah), you have an embarrassment of riches in terms of enviable quality produce to choose from.
5. If you're saving a lot of money vs restaurants at our level, you can probably afford better ingredients which will make a big difference, especially with good produce. Exceptions are Aldi Sud (Aldi) or Nord (Trader Joe's) or Lidl when they show up as they sell reasonable quality for reasonable prices. German basic groceries are a godsend overseas.
6. If you want to get good at technical cooking, French/Belgian, Indian, Thai, and Italian tend to force you to be multitalented in technique where other cuisines are more forgiving. But unless your technique is exceptional, good ingredients that the US has almost always can make up for bad technique to be at least edible.
When you see Kobe beef in the US, it almost always refers to Kobe style American beef. It doesn't come close to the marbling of Japanese Miyazaki Wagyu beef which melts in the mouth. Price difference between American Kobe and Japanese Wagyu can also be 40/lb vs 120/lb.
However, I think a dry-aged prime ribeye or porterhouse done perfectly medium-rare from a good NY steakhouse can be just as enjoyable. They're also more likely to get first pick at the best cuts from domestic meat purveyors. I've been to the Vegas outpost of Del Frisco's and found that they have a tendency to overcook their steaks compared to the Manhattan one.
Absolutely, though I have a taste for Texan beef which is the opposite of marbled. I completely agree with your assessment on overcooked meat in Vegas. WagyuSA beef from the US though is nowhere as finely marbled as the genuine article Wagyu. Then again, there are times the melt in your mouth feeling is exquisite.
I find that when you're in Vegas, most of the chefs have international tastes in mind, so overcooked beef, stewed vegetables, al dente pasta (most Americans seem to prefer their pasta well-done). The one thing about Vegas that is decent is that their Italian baseline is far better though definitely not on Chicago, New York, or New Jersey competency.
