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If my opponent has a unit high up on top three-story building when I deploy my 'deepstrike' reserves 9" away do I measure true distance vertical/horizontal base to base or do I measure from my opponents model top down just horizontal distance.

I think the only time it came up was early 8th for me and i did the latter but I saw recently someone at my local game club do the latter, on reflection i feel it would be the former: base to base vertical and horizontal essentially putting my unit near the first floor, as opposed to, being 8" away from the first floor.

Not sure what the "correct" answer is here, but we've been playing it as the former since we consider the deepstrike rules to function similarly to movement rules

A straight line between the two closest points on the Hulls/Bases, for that is how we normally measure distance between two objects by default and best follows the instructions on page 176.
The Rules for Measuring Movement, requiring Horizontal and Vertical to be added together, are a special little snowflake that exist because of Developer Commentary not letting the damn thing die.

The 'top down' thing is a phenomenon exists due to the fact Game Workshop has never considered the third Dimension all that well, though this was noticeable in past editions involving more complicated pieces like Templates. This 'top down' method works so very well because that was how those Rules are written. Nothing but a single Model interacting with another single Model on a flat tabletop was taken into consideration when the Basic Rules where written, and many more complicated ones as well. That makes Rules which do work best within flat representations, is the sole reason that Bases exist, is why many Rules are explained using top-down pictures, and why the game simply plays better in 2 dimensional environments such as Vassal.

What little Rules we have involving the third dimension have always band-aids at best, slapped on to cover a specific situation before we go back to ignoring the Vertical.
Like that before mentioned and forever cursed to never die Rule for Measuring Movements....

Long story short:
Measure along the hypotenuse, unless otherwise told to do so.

 SebboVonTebbo wrote:
If my opponent has a unit high up on top three-story building when I deploy my 'deepstrike' reserves 9" away do I measure true distance vertical/horizontal base to base or do I measure from my opponents model top down just horizontal distance.

I think the only time it came up was early 8th for me and i did the latter but I saw recently someone at my local game club do the latter, on reflection i feel it would be the former: base to base vertical and horizontal essentially putting my unit near the first floor, as opposed to, being 8" away from the first floor.

As always, unless specified otherwise, you measure base to base (so holding the tape measure diagonally in this case between the models on the ground and the models up on the building).

And yes, this can mean if you wanted to move into contact with the enemy (charge them) you'll have to move much more than 9". This makes putting models up on top of terrain to block 'deep strike' units that want to charge a very good tactic to use.

This is also why grapnel launchers on reivers are extra cool