I know your question is about pedals, but that might not be what you actually want to look at.
But the clean tone of my guitar discourages me so much
I want a bit of punch and crunch. The Frontman has a built in Overdrive which helps, but what else could I look at?
The first thing I thought of when I read your question is that you should strongly consider upgrading your amp to a low-wattage 1x12 all-tube combo amp, instead of buying pedals at this time. A quick search on Sweetwater.com shows that Fender, Marshall, Supro, Vox, and Blackstar all make amps with those qualities for under USD 700. Before you decide that $500 - $700 is more than you want to spend to improve your tone, consider whether you might end up buying more than four $100 pedals in the search for a better sound, all which would could be held back by the tone of your Frontman.
I started playing guitar with literally the cheapest amp they had in my local music store. Like you, I quickly became frustrated that I just couldn't get the sounds I heard on records from my first guitar and amp. I bought a Boss BD-2 blues driver pedal and a Dunlop Crybaby wah pedal, but that didn't make me very happy. After saving everything for about two years (I was in college and working fast food part time), I was able to buy a Fender Blues Deluxe amp and everything sounded much better. With that I was able to get some excellent tones, and I've had that amp for 25 years now. I've used it on gigs and recordings even after buying a boutique amp (which I love also) about 18 years ago.
The reason why I suggest not merely adding pedals with the Frontman is that the Frontman will impart its sound on everything that runs through it, so pedals might improve things a bit but there's always going to be a limit on what you're hearing from your guitar until you get a quality amp. By upgrading your amp first, you not only improve your sound right away, you also create a much better sonic environment for whatever pedals you want to add later.
Thinking about the journeys of myself and my students, here is how I would recommend moving through the process of purchasing gear as a guitarist over the years.
- Start small and affordable - decide to commit to guitar or not before spending a lot of money (you are already done with this step) - BTW in my experience the Squire guitars are great for the price and you can hold off on replacing it until you really know you want a different guitar
- Purchase a 1x12 tube combo amp - low wattage is good for keeping it home-friendly. An alternative is an affordable amp modeler - upside is you can practice silently with headphones - downside is it will become obsolete while a decent tube amp is a lifetime musical instrument
- The first pedal I'd recommend to anyone is something in the overdrive/fuzz/distortion/boost category. One way to go is copy your guitar hero(s) on this (e.g., as a huge Jimmy Page fan I should have, but didn't, look for a Tone Bender clone much earlier than I did). A pedal like this really gives you a lot of options to create different tones, especially when combined with a good tube amp.
- After that it starts to get more specific to genre and playing style. For many styles, a compressor is a good way to go for a second pedal. Other styles might be helped best by a wah, phaser, flanger, chorus, delay, or even another flavor of OD/distortion/fuzz/boost.
- At some point, you'll probably get a sense of when your guitar is holding you back. Unfortunately it is my strong opinion that the guitar itself is very personal and you really should try before you buy so you can tell if it feels right for you, and while the pandemic lasts that is not so easy to do.
Repeat as needed/desired. Buying used is great although for the first couple purchases in each category, it's really nice to be able to go to a store and actually play the different options in your price range.
Regarding digital anything: Digital stuff does become obsolete. Sometimes it takes longer, sometimes not so long. Most analog stuff becomes vintage with enough time, but either way it's very rare that an analog design comes out that is clearly superior to a previous analog design for the same purpose. I suggest that digital guitar effects, amp modelers, etc. are the perfect tools for working and gigging, but can be frustrating for finding your personal tone, playing for your own enjoyment, and building a life-long collection of gear.
The exceptions are the categories of time-based effects. This includes delay, reverb, chorus, flanger, pitch-shifting, looping, and few other less common effect types. While most of those effect types are available both in analog and digital form, and the analog versions often have a lot of character (and higher cost), the digital versions are generally very good and also have a lot more longevity. There are a few digital effects that have such a character and quality that they have become vintage instead of obsolete, including the Digitech Whammy Pedal and the Line 6 DL-4. The digital effects that I find to be the weakest are the amp simulations (although those have become very good lately), distortion/OD/fuzz/boost, and compressors. At least for the last two categories, there are too many excellent affordable analog options that there's no need to go digital for them unless you really need a small footprint for the stage or orchestra pit.