#1 is getting stuck rolling a tool. Larger diameter wheels help here.
Using a roller stand can be a bit tricky, but usually these can be adjusted to correct.
My floor is "ok" as far as pits, but does have some low spots. The biggest concern was the table saw with the 52" fence. It is on a mobile base, but I never move it. Potential problem is twisting in the mobile base when parked. To keep the extension table even with the main saw table. I have to use adjustable feet to get it all coplanar which is kinda critical.
Other tools are probably fine as long as they don't rock or roll away to a far corner of your space.