Skynet was losing the war. Sending back Terminators to try and change the outcome of the war was a last ditch effort. As such, Skynet probably couldn't afford to wait until it had developed a newer, more powerful terminator.
Not to mention, the T-1000 (Terminator 2) was an "advanced prototype" (according to the T-800/101), implying it hadn't even been tested in the field before being sent back. That is a sign of desperation in itself.
In T3, we learn that Skynet was delayed (not stopped entirely). But this also meant that Skynet started with more of a leg up than before. It had the time and the resources to develop better assassins (the T-X).
However this was a different Skynet to the one originally under development (Skynet 1 had a central control point, Skynet 2 was a distributed application in cyberspace). Why is this important? Because Skynet 2 didn't know about the earlier failed plans and therefore couldn't know to send back better Terminators for reinforcements. It originally sent back the T-X to take out John's lieutenants, as John was off the grid and couldn't be found. (It was only by pure luck that the T-X found John).
In conclusion, Skynet 1 didn't send reinforcements back because it was losing the war and either didn't have any, or lost control of the time-travel apeture too quickly, and Skynet 2 didn't send reinforcements back because it wasn't aware of the earlier assassination attempts, and couldn't find John anywhere as he was off the grid up until the events of T3.
SkyNet shouldn't care about a timeline
- Sorry, but why do you think that? Surely SkyNet would make a point to avoid doing things that would negate its existence, or change things.