You can come up with a lot of ideas if you think about why people stay put in the first place. In a very real sense this has to do with Labor Specialization and supply chains.
Where things get made is determined a lot by local resources. If the local resource is good soil and water, then Farms sprout up. Farms have to be tended to though and that means people stay put. Coal is another example. the coal doesn't move around so if you want it, you have to dig it out and that means you stay put. If you want to produce more than can be used by your clan then you have to trade for other things as your time is spent digging up the coal. You trade with the farmers for their surplus food and now they can use your surplus coal to stay warm in the winter. All of the sudden you have a rudimentary economy (basic barter for two resources that don't move), a supply chain (moving the surplus back and forth) and specialization (coal mining and Farming). Thists a massive over simplification but it outlines why humanity moved away from Nomadic lifestyles in the first place.
By forcing people back to a nomadic lifestyle, you will in essence take away specialization on any large scale. The only things your people will be able to keep is what they can carry and maintain while moving around. Sure, some specialization will take place within the tribe, but it won't be anywhere near the levels needed for any kind of sophistication. Even if generation 2 has all the benefits of modern tech, they will lose an awful lot of that as survival takes precedent. The benefits of technology only make it while the machines work. Batteries lose their ability to hold a charge over time. Seals in internal combustion engines degrade. Wire insulation breaks down leading to short circuits. You can't really maintain anything but the most simple things without the ability to get parts, and that requires a supply chain, which means people somewhere have to stay put. In a few short years, people will be much more focused on simply staying warm in the winter and having enough food. They won't have the time or the inclination to try to keep the digital library intact. Added to that, having information in hard copy is too heavy to carry. A few books is heavier than a lot of different kinds of weapons and when you are hungry, that book on electricity is useless. Knowledge is powerful, sure, but it is secondary to survival.
Not all books are useless. One on edible plants and medicinal plants would be treasured, but accidents and entropy would slowly remove a lot of the copies.
By around Generation 6 most knowledge that is not directly tied to survival in some form or another will be lost. Working items from the time of the first generation will be almost entirely gone. The few that remain won't be understood. Anything that cannot be done on the road, or in the span of about a season will be pretty much gone.
Your end result is that you will probably drop back to early iron age technology. Blacksmithing is a useful skill. The tools needed are portable or can be made on site. Iron ores, oxides, and so on are all over, at least on earth. Early anvils were most often a big rock. The first hammers were also rocks. Early iron in some parts of the world came from peat bogs. Charcoal is available anywhere you can find wood. Most importantly, it is a skill where you learn more by doing than by reading. The clan's smith can teach children who are not quite old enough to join the hunting parties. Not all of them will take to it, of course, but almost all of them would probably learn enough to make things like arrow heads pretty early on. The small number who do take to it would carry on the tradition. The new smith would be valuable to the clan in a way that would allow them to specialize long term. The lore around metalsmithing would probably not change too much because the nature of iron does not change.
So your tech begins to lose relevancy around about Gen 3. By Gen 6 most techs and knowledge are gone or polluted. A few fields of study remain. Enforced Nomadic lifestyle means that any meaningful supply chain never gets built, so by 1000 years you have a race of iron age roaming tribes.