I’d start with a few older pressings of preferred content, a few in good shape, and see how they strike you. Much different from CD/digital stream on your setup? If it seems promising, then find a new pressing / “audiophile” pressing of the same performance and see which you prefer, again, if difference is discernible to you. On a given system it might not be such a remarkable difference. Or to a given listener. Older stuff wouldn’t have been remastered, which may or may not be a good thing depending on your taste.
Record cleaner - they now have an acrylic disc for each side of the record label that both tighten together with screw knobs - it’s like a compressed dough-rolling pin you hold on either side of your record through the spindle hole. Silicone discs attached to each facing acrylic disc to keep water off the labels. Like corn-on-the-cob spike holders that waterproof the labels. Make sense? Anyway, it makes it so you can blast both sides / all grooves with high water pressure - the way they do it at pressing plants. The secret to clean grooves without paying much is permitting high water pressure. I prefer that route to a $4.50-per-record fee, but I’d also wager more than $4.50 that @ghdprentice machine gets less water on your countertop while in use.
Those Ortofon 2M cartridges are fun, and money well-spent IMO. Again, if your system lets you hear difference between models enough to justify the price hike between them.
x2 on the Half Price Books option. I bought many classical albums there for $1, many new sealed in the shrink, never opened by the person who’d bought them. That comment about family having to resell vinyl at a loss someday is potentially very real. I bought many a shrink wrapped record with a $2-5 “great deal” original promo sticker price tag, with Half Price’s little yellow $1 rectangle stuck on over it!