Run length for a given wire size is generally limited by the voltage drop across the line when under load. No more the 5% off nominal = 114V minimum, though I have not seen any electrician care about this in my area. Other things that can impact wire size are deratings due to number of conductors in a conduit (likely not a problem for you now) or maximum expected ambient temperature.
NM-B (Romex) is permissable in crawlspaces, assuming no local restrictions. If using conduit, you cannot use romex and must run individual THHN conductors.
Some other concerns: You swapped from an outlet without a neutral to one with a neutral. Devices hooked up to a 14-30 (or any 14 series) can expect to get 120V between a hot and the neutral conductor. Not having this available can cause catastrophic failures. Was there a 4th wire in the wall already, just not hooked up? If not, you really need to put the 10-30 back on.
The problem with breaker sizing is you need to assume the entire lenth of wire is up to code for 30A capacity. It is bad practice, but not generally against code to mix wire sizes (assuming splices are in boxes, etc...) on a run, as long as the breaker is sized to the minimum capacity of wire in the circuit. If you can't inspect the whole run, I would be very hesitant to move to 30A breakers.
30A outlets on a 20A breaker are a code violation though, as 20A outlets exist. Only exception I'm aware of is 50A outlets on a 40A breaker.