I am a hybrid woodworker so I am already where you are heading. I see from your opening post that you are already prepared for the onslaught and variety of responses. This is a good thing. Here's my take if I were to go back and do it again. I can barely squeeze into a medium Wells Lamont style work glove and a large is what I wear just to give you an idea of hand size:
#1 Block plane - Varitas Apron Plane. I have other block planes, all very good ones. The Apron Plane is my most used and the one I would keep if I could only have one. I find the DX-60 awkward to hold; right shape, wrong size.
#2 Smoothing plane - I have a couple of No 4's (actually Millers Falls No 9's with PM-v11 iron / cap sets) , a Veritas BU smoother and a Veritas Low Angle Smooth Plane. If I could only keep one it would be the No 4. This is influenced by my owning a Veritas LAJ as mentioned in the next section. If I need a steep or shallow angle smoother I just pop the appropriate iron in the LAJ. YMMV.
#3 Jack plane - Veritas Low Angle Jack. I love this plane. It smooths, it joints, it shoots. My affinity for this plane is akin to a Festool user choosing their router; there is a herd-benefit that may not be present if used alone. My LAJ, my BU Smoother and my BU Jointer all take the same iron size. I have a half a dozen that I exchange between them making all of them multifaceted in their use.
#4 Jointer plane - I run a Veritas BU jointer for the reasons stated above. If I didn't have the herd-benefit of swapping irons . . . I would still get the Veritas BU Jointer. The Norris style adjuster, the set screws, the stop for the adjustable throat; all these combine to make taking the iron out for a quick touch up and then going right back to work effortless. These features also allow me to swap iron angles to the task with minimal adjustment. *** not a determining factor *** There are also a selection of add-ons (fence, variable angle fence, fast adjusters, different totes and knobs) for the BU Jointer that may help the user when starting out and beyond.
IHMO, the Woodriver planes have priced themselves so close to Veritas or Lei Nielsen that I wonder why one wouldn't just cough up another "bar tab" and go for the head(s) of the pack.
"A hen is only an egg's way of making another egg".
– Samuel Butler