Hate if you will, but I say planning to immediately upgrade to a bigger turbo on the car you literally just bought, which happens to have 141k miles, might not be the best plan of action. Then again, you were running a KO3 @ 22psi, so maybe you're not concerned with the longevity of your cars and associated parts.
Why not do this modding in steps ? : Do a TBE, 255 Walbro, and tune, and see how you feel after that. The extra 50hp (give or take) might be just what you need. If that doesn't do it for you, swap in the vf39, TMIC and injectors and re-tune. BTW, 440's are the stock injectors for your WRX.
Nothing about a VF39 makes it safer for high mileage cars when compared to other turbos (unless your other options are 20g, FP etc.), IMO. It may change how and when the car gets torquey, and be nicer to your tranny because of that change, but overall when I think "longevity", I don't have the list that you produced coming to mind. I'm not sure what your goals really are, as you're saying "safe daily on low boost", but the first desired mod you list is an upgraded turbo and everything to support it.
This thread is going to be chock full of opinions, so I'll give mine: I'd be really nice to that WRX if I were you, because it's def high mileage, and while it MAY run for years and years in modded form w/ no issues, it's less likely than the other possibilities.... Pretty much everyone suggested that you look into brakes, tires, sways, etc. All things that will make your car safer, and offer a enhanced driving experience when tearing-ass around.
My 2 cents = Stage 2, and some tire, brake and suspension / handling mods.