Here’s a summary of Steam games with the most paid DLC by sheer count — split into two lists you asked for:
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Top Games by Number of Paid DLC Priced $9 or More
There isn’t an official Steam-wide ranked dataset publicly available that breaks down DLC counts by price threshold, but based on community tracking and known large DLC catalogs that mostly include $9+ DLC items, the following titles are among the highest:
1. Train Simulator / Train Simulator Classic — hundreds of paid DLCs ($19–$40+ each common). Extremely large catalogue of routes, trains, scenarios.
2. Rocksmith 2014 Remastered Edition — Thousands of song DLCs (often priced ~$2–$4, but many song packs and premium songs were $9+ historically and counted as paid DLC).
3. The Sims 4 — Around ~80 DLC packs including game packs, expansion packs, kits — many $19.99+.
4. Cities: Skylines — 40+ DLCs with many priced $9.99+; large expansion packs add major gameplay features.
5. Dead by Daylight — 45+ DLC packs (chapters often $9.99+) adding killers, survivors, maps.
6. Crusader Kings II / Crusader Kings III — Paradox strategy titles with dozens of DLC expansions (most $9+).
7. Europa Universalis IV — Dozens of paid expansion packs, many $9–$19.
8. Monster Hunter Rise — Many titled expansions/content packs (varies by release).
9. Microsoft Flight Simulator X (Steam Edition) — ~200+ aircraft/scenery DLC (many $9–$20+).
10. Dead or Alive 6 (and similar fighters) — Many character/season DLCs often priced $9+.
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Note: Counts change over time as new DLC are released (especially for ongoing live games), and exact listings by Steam store API would be required to compute precise current totals per price tier.
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Top Games by Number of Paid DLC of Any Price
These are known from community sources to have the largest total number of purchasable DLC items on Steam, regardless of price:
1. Train Simulator / Train Simulator Classic — ~700+ paid DLC items historically tracked (routes, trains).
2. Rocksmith 2014 Remastered Edition — Over 1,000+ DLC items (individual songs & packs).
3. The Sims 4 — ~80+ DLC packs.
4. Cities: Skylines — ~40+ downloadable packs.
5. Dead by Daylight — ~45 DLC chapters.
6. Crusader Kings II — Dozens of DLC.
7. Europa Universalis IV — Dozens of paid expansions.
8. Monster Hunter Rise — Numerous paid content bits.
9. Microsoft Flight Simulator X (Steam) — ~230 paid DLCs.
10. Payday 2 — ~30+ DLC packs (heists, weapon packs, characters).
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Notes & Clarifications

On counts:
DLC totals can include expansions, packs, character packs, cosmetic packs, route/tracks, music DLC, etc. Most community lists count every unique DLC entry visible on Steam.
Train Simulator and Rocksmith dominate due to modular purchasable content (each piece sold separately).

On pricing tiers:
It’s hard to filter DLC counts by exact Steam price (like “$9 or more”) without live Steam API data. The above $9+ list includes games where historically many DLC items are full priced ($9.99+).
Some titles (like Rocksmith) have most DLC cheaper than $9 each but also had pricier bundles historically.
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Quick Summary Table
RankMost Paid DLC ($9+) Titles (Estimated)Most Paid DLC (Any Price)
1Train SimulatorRocksmith 2014
2Rocksmith 2014Train Simulator
3The Sims 4The Sims 4
4Cities: SkylinesCities: Skylines
5Dead by DaylightDead by Daylight
6Crusader Kings II/IIICrusader Kings II
7Europa Universalis IVEuropa Universalis IV
8Monster Hunter RiseMonster Hunter Rise
9Flight Simulator XFlight Simulator X
10Dead or Alive 6Payday 2
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If you want exact current DLC counts pulled directly from Steam’s database for a custom list (e.g., “every game with >20 paid DLC”), I can help build a script or use Steam API to generate that dynamically!