Mark (Tactical Painter) wrote straight-up in the lead paragraph of his WSS Scratch-building article -
"As much as I like my terrain to look as realistic as possible it also needs to work in the context of the rules that I am using and in the way my figures are based."
Great advice, along with demonstrating some superior crafting results.
Sometimes it's the Wild West trying to get rules-suggested basing, or gaming ground scales to work with commercial, off-the-shelf buildings (especially if the buildings also contain yards, walls, crop allotments, etc. on their own bases – details nice to have, but sometimes confining for 'figure management').
There's a few game companies that offer terrain, minis, rules, and scenarios that all work as a package-deal for some of these historical game periods – a new one that comes to mind is Voxel House, who does this for WW2 in the smaller, battle-scales (great if you've got a 3D Printer, or can solicit and order via Print On Demand from the Voxel House STL files).
Warlord Games does this type of models-to-rules integration, and of course it's the business model for what has poured forth from Games Workshop, and their fantasy sci-fi-supplied genre games.
We here as fans of historical miniatures gaming have to scramble quite a bit to get some of our favorite periods to unfold onto the tabletop – sometimes that's a point of pride, and part of years of experience – still, it's a hurdle that many new gamers interested in historical gaming have to fast….there could be better integration (or more package-deals for this side of the hobby for sure).
Maybe it's conforming to the 'company rules', and having gaming collections designed to work with those company products that strikes a sour note to the independently-minded gamer, who likes to try out new rules (say – outside the Big Box game systems)?
In the meantime, there's still a lot of game craftiness that comes along the way with this hobby – that being both good and bad (though, I think for the younger generation coming up, this could be a hinderance to getting into the historical side of gaming).