For safety's sake I like to stay as close to the book as possible.
In the case of cast handgun bullets I'll stick with common designs like the Keith bullets or target SWCs or Cast Performance big-meplat bullets. These vary some in weight, design, and hardness, but the load data seems to be pretty forgiving so long as I pick a bullet that is very similar to one I have data for.
One thing I find helpful is to use a Loadbooks USA book for my load data in, say, 44 magnum. Those books have load data for just about every bullet combination so I can always find something so close that I can be confident in the safety of the load.
As for specifically loading a 255 grain bullet with 250 grain data, I personally would be OK with that so long as the design and construction of the two bullets are very similar.
I am less flexible about varying jacketed bullets in high-pressure cartridges because some bullet designs look similar but are different enough to have significant pressure consequences if you use data not intended for them. For example, bullets that weigh the same, but one has a longer bearing surface than the one I have data for. I like to use the manufacturer's data. I even use the same brand and model of primer as specified in the data for my rifle handloads.