Espresso is a big learning curve, especially if you want to get good at milk steaming, but the end result is fantastic once you get the hang of it.

I bought the 2019 model of the Gaggia Classic Pro earlier this year and really love it. I have a lot of prior experience as I was a manager and barista in a specialty coffee shop for a while, so that definitely expedited the process of learning how to get great results out of the machine. You may not have that experience to go off of, but there are a ton of great resources online for learning.

What grinder do you have? There's a good chance you're grinder may not grind fine enough or consistently enough for espresso. The one thing a lot of beginners underestimate when getting started is how important it is to have a good electric burr grinder that's made to handle grinding for espresso. Those can cost a lot of money and generally run $300+ for entry level espresso grinding. All that said, for just getting started, I think it's totally fine to have your local coffee shop grind your coffee for espresso while you start learning the process.

I'm not sure how the Evo comes set up, but the older model was not set up for espresso enthusiasts but rather consumers who aren't looking to get too deep into it. As a result there were a couple upgrades that I found necessary out of the box; namely the tamper was just a piece of plastic, the portafilter came set up as a pressurized portafilter so I had to remove that piece of it, and the machine was set to 15 bar pressure so I had to switch out the OPV spring to get 9 bars. The Evo machine comes set at 9 bars out of the box so you won't have to worry about that. I'm not sure about the tamper/portafilter situation though.

Espresso is a blast one you get the feel for it! Let me know if you have any other questions, I'm happy to help!

A gaggia seems nice and you can upgrade it later with https://gaggiuino.github.io

I'm not sure what your budget is but sometimes the extra money over the period of two to three years doesn't seem so bad. Apparently you have to shim the MD15 to grind finely enough, it suggests that you might over time want something a little better, but otherwise it's a reasonably cheap starter burr grinder. There is a noisy grinder which been be bought cheaply which did a pretty good job, the Iberital MC2, but on the whole, a good grinder is going to set you back as much as the EVO. It could well be worth looking for second hand equipment, as this is usually available when people upgrade. I have a Eureka Mingon and I find it to be very good. The only drawback of the mignon is that it's not easy to switch back and forth to different grind settings (for two sets of beans) but it is possible. It would probably be at least double the cost of the MD15, but see if you can get any deals. If you get the crono, which is probably the cheapest mignon, you would also want the espresso burr set to switch out, which is not that expensive and will grind as fine as you need.

~~I don't think I'd recommend that machine. Simply because it's not a portafilter.
In these automatic machines coffee grounds get stuck in all sorts of nooks and crannies.
In my experience people don't run the daily cleaning program nor the weekly one. And even you do, some coffee grounds stay behind so you always have old coffee grounds in the path, affecting the taste of your coffee.~~

I looked at the Accademia series. Completely different beast.

The Classic Pro Evo looks like a nice little beginner's machine. Not too dissimilar to my first machine, a Rancilio Silvia.

The EVO has a teflon coated aluminium boiler. This should prevent pitting and corrosion in theory, and with no abrasive action on the teflon should theoretically last a long time. The use of descalers should be checked for the effect on the teflon coating of the boiler. The non-chromed group seems like a minor improvement. I think this is a good choice for a keen espresso starter, but I would look for a decent grinder too.