Assuming you have a Technics SL-D33 turntable now, I’d say you ought to look at a new turntable and phono stage first. Subwoofers are a dodgy proposition at best. Plan on upgrading your speakers after the turntable and phono stage.
You need to to decide what functionality you want. In my case, I did not want a fully manual turntable, because I wanted automatic tonearm return at the end of play. That narrowed down the field considerably to vintage semi-automatic turntables. I bought a Technics SL-1700mk2 and restored it with a few upgrades including an Audio-Technica VM540ML. I upgraded my NAD PP2 phono with a Burson V6 Classic discrete op-amp and custom built regulated power supply. All in, I’ve invested about $1300 and I’m very pleased with the results. Hope this helps.
You need to to decide what functionality you want. In my case, I did not want a fully manual turntable, because I wanted automatic tonearm return at the end of play. That narrowed down the field considerably to vintage semi-automatic turntables. I bought a Technics SL-1700mk2 and restored it with a few upgrades including an Audio-Technica VM540ML. I upgraded my NAD PP2 phono with a Burson V6 Classic discrete op-amp and custom built regulated power supply. All in, I’ve invested about $1300 and I’m very pleased with the results. Hope this helps.