As I said, shooting analog film might not be a delight. I also teased that there might be a way to fill that "creative gap", and that is adapting old lenses to your digital camera. Depending on the model you have, the possibilities are almost without limits. I think that re-using these well-crafted pieces of glass and metal is often overlooked, and undeservedly so. Below, I share what you should watch out for if you want to enjoy the "analog" feeling on your digital camera.
Adapting old lenses first and foremost also means adapting your workflow, because you will have to abandon some of the commodities of fully digital photography. Most adapters also have no electronics, and that means your camera does not know anything about the glass in front of its sensor. Consequently, all programs that employ lens electronics do not work, i.e. time-priority shooting or full-auto mode (because setting the aperture does not work). You may have to force your camera into actually actuating the shutter when it thinks there is no lens attached. There is a setting for that in the menu, usually.
Perhaps the lack of features is perceived as a downside at first, and it means that you (have to) get more involved in the process of taking photos, and that is a good thing to me. I've talked about creative consciousness before. Adapting old lenses forces you to do so by limiting the access to auto programs of your camera naturally.
The next step back might have the biggest impact to your workflow and that is: No autofocus. Old lenses have no motor driving the focus ring, which should be obvious when no electronics are present at all. Just thought I say it out loud again. And I'll be honest: Manual focusing is painful, especially on non-full frame DSLRs. You literally judge sharpness only from the matte plane in the viewfinder. With mirrorless cameras (and hence the presence of LiveView or EVFs), focusing got easier by several orders of magnitude. You can zoom in and check focus easily.
So there is my first and most important recommendation when it comes to adapting old lenses: Get a mirrorless camera. You won't have much fun otherwise.
Old lenses have many appealing traits. One of them is the variety and the availability at relatively cheap prices (with exceptions). Finding out whether old lenses are for you is not an expensive experiment. All you need is literally an adapter and a lens. Since you buy them used already, losing money is not so much a risk because if you sell them a month later you won't lose big money.
Also, with the variety of lenses available, you'll get a variety of looks. I recommend reading a lot of the (now available) reviews of lenses to get an impression whether the lens fits you desired look (or, a step easier, produces a look you like and you want to try).
Of course, it's not all light and sunshine. Some lenses from the old days are just... not good. That is part of the whole story and worth mentioning. Some glass resolves poorly, i.e. cannot produce sharp images. Some have heavy color casts, others are garbage in terms of haptics.
And: If you have a DSLR, some lenses may not fit your camera. Especially with wide angle lenses, the rear element reaches too far out into the mirror of the camera, which causes the mirror of the DSLR clash against the lens element when the shutter is pressed. Worst case is that the mirror of your DSLR cracks, because it moves at quite some speed. With mirrorless cameras, that problem practically disappeared, which is also why I recommended getting one for old lenses.
So why is it better than shooting film? Well, you simply don't have to face the struggles with, and perhaps the high initial cost of getting into film. Only a new lens, and not a whole new system means that you also stay on familiar ground because you just have to operate your camera slightly differently than normal, i.e. switch it to manual or aperture-priority mode. You don't have to get used to a wholly new tool.
Also, if you are disappointed with the results, you just have to resell the lens, simple as that. I don't want to know the amount of photographers investing big money in analog gear, only to find out that it's not for them.
As I mentioned in previous essays, the learning curve is also important, i.e. making mistakes fast, and at low cost. With film, any shot costs money, specifically also the failed ones. With digital images, you are liberated from that "threat", and you can experiment more. Also, the immediate feedback is very helpful, because adapting lenses also often means that you have to adapt to the lens. All that is achieved at greater ease with digital image caption.
In turn, you can get top-notch optics at rather small prices, and a unique look from them (which is what you are here for ultimately, are you?). A lot of a photo's look is determined by the lens, because it is simply the first thing that comes between reality and the capturing medium. It essentially has to project reality, and that is a very influential task. Hence, the variations in look among different lenses are so big, because the first step in the (creative) chain determines the general direction.
In contrast to modern lenses (sometimes perceived as "clinical"), old lenses often use simpler a optical formula, simply because of engineering and simulation/calculation limitations in past times. That results in its own look, which a lot of people (often wrongly) attribute to analog photography. Their characteristics, and also their imperfections in rendering are often described as "organic". But again, it is a unique look, for each lens, and that is what provides such a fruitful source for creative work.
In the end, it's all preference when it comes to looks. That especially holds true for which lens you are going to choose. In any way, old lenses offer great potential as tools to express yourself creatively. With artificial intelligence producing perfect, clean images, it may just the imperfection, the "character", and the "organic" look that delivers what you long for.
Because of all that, it is very hard (read: impossible) to make a recommendation of which lens you should get as a start. I also left out quite a fair bit of the brands because I found my dream combo early. And to this day, I have not yet experienced a longing for something different. It may change, but for now I'm settled.
In addition, I had to realize that no gear review of anything was helpful to me in the end, in the sense that I could confirm the reviewer's point of view, or sometimes come to an even remotely similar verdict. I could make that a whole new essay...