...Secondly, can i use velocity as a pressure indicator? Lets say im working up a load for one of these odd-length bullets. I load it to 2900 fps. I know that the shorter bullets of the SAME WEIGHT can be fired safely in this caliber at ~3000fps. Does this mean i can keep adding more powder until i reach ~3000fps with the longer bullet? (lets assume i don't see any obvious signs of excessive pressure).
Yes you can, although we're talking about estimates, not absolutes.
Even commercial pressure testing equipment provides an estimate (margins of error, differences in equipment, etc.), and the estimate is for that day, with that powder lot, with that primer, with that chamber and bore, in those climatic conditions, etc. "Pressure Signs" are notoriously deceptive and unreliable, and cannot be trusted, although I'd say a blown primer pocket is a sure sign of very high pressure and to back off (but I can't estimate what the pressure might have been very accurately). Casehead expansion could provide a good estimate, but only if you possess baselines to measure against, consistent brass to measure, and a very accurate and consistent measuring technique.
Muzzle Velocity (MV) however, can provide a useful, reliable and practical estimate for anyone with a Chrony, and the thought process you are following is sound - I've followed it many times.
Once we have a published load (including pressure), we are free to substitute slower powders, and we have a benchmark to let us know when we're moving into higher pressure territory. We know that if you require more of Powder A to produce the same MV as Powder B, that the Powder A load is operating at a lower peak pressure. If the load book shows a load for H4831, but not for H1000, I can try the H4831 load in my gun with my components, note the MV, and then safely substitute more H1000, knowing that for the same MV, the peak pressure is lower. Conversely, if I want to use Reloder 15, if the MV is the same as for H4831, then the peak pressure is higher. You won't know what it is, but you will know where it falls relative to H4831. You can't do that by looking at primers, nor by measuring casehead expansion.
We also know that a heavier bullet will generally produce a higher pressure and lower MV than the same load with a lighter bullet. Even bullets of the same weight, over the same load, will operate within an MV range, but not necessarily the same ranges, e.g. one might show 2850-2925, and the other 2890-2965. There's a lot of overlap there, but the one range is notably higher. Higher pressure is but one explanation, others include less friction due to less bearing surface or a more "slippery" coating. In this case, if the published load had a slower MV than that for the substituted bullet of the same weight, I'd back off the load a bit for the substitute. You can't do that by looking at primers, nor by measuring casehead expansion.
Some guys will just say "If it's not in the load book, don't use it!" or something dramatic like "It's your face!". Those guys should stay safely within what their books say (but books vary, so which book?), but a thoughtful, careful reloader can safely do what you have suggested.