Flair Classic Espresso Maker

Flair classic + kingrinder is probably your best bet!

Additionally I would recommend one of the Flair machines with preheating built in. I started trying to get into espresso with a classic flair and all the extra steps before hand just lead to me never actually using it.

Second that. Lever machines have the advantage that you can always control the pull and more importantly you get feedback. So you can control the pre-infusion time and ramp up/down the pressure with the lever. This is really helpful if you plan to brew medium or light roasts which are not forgiving as darker roasts. I don't know if you have the same level of control with the Picopresso. Users have reported on Home Barista that they observed hissing sound from the top when they grind finer. I have used the Flair Classic and they make pretty decent espresso. Controlling the temperature was however always difficult. Preheating works in principle but since metal dissipates heat, you can never predict the temperature of the water hitting the puck. Which means, achieving consistent results would be a challenge. I guess this is the case for all manual brewing machines including the Picopresso. As it is your first espresso machine, I doubt if you'd notice the difference in shot quality between both the brewers. However as your technique and taste pallet evolves, you'd most likely buy better machines. In such a case you could always keep your Picopresso as a nice portable brewer to carry along.

The Flair workflow is a pain, especially when making multiple drinks. I have one and a La Pavoni and the Flair only gets travel use. (Edit: Didn’t realize the 58 has a more “normal” workflow than the classic Flair). I bought my mom a Bambino Plus + Sette 5 years ago and she absolutely loves the setup. The machine hits a real sweet spot as a step up from a Nespresso, as the instant heat is EXTREMELY practical for exactly your use case (early morning pre-coffee caffeination), to the point where I’m shocked that nobody has really nailed that in the “step-up” machines. There are better grinder options today, and you have some choices with the machine (you can find a second-hand La Pavoni around that price range, or any of the options you listed). If I were to swap pieces of my setup for my mom’s, I’m fully confident I’d get a similar (or perhaps better) shot out of her machine with my grinder, but the gap between her Sette and my Mignon XL is serious (though the price sweet spot may be somewhere in the middle).

39mm classic was always easier and more consistent for me. Shots did not taste inferior at all. However, workflow for multiple shots and cleanup were easier for the 58 (I had 2 shot kits for classic). I split the difference with the stamped 58-49 step down from Sworks and custom tamper from Etsy. My grinder was happier as well (SSP Cast V3 couldn't fully pressurize lighter roasts at chirp for 58mm).