I was the editor of Dr. Dobb's and am currently the editor of Java Magazine (from Oracle). I get hundreds of pitches a month. The triage greatly favors outreach about products in my site/magazine's wheelhouse and initiated by someone I know. The latter bit is key. If my contact is at a PR agency that I've worked with before, I know they know my coverage area and my interests. But mostly important, I know their client will be prepared.
This means that if I ask for a demo, the guy doing it knows how to do a demo. I also know the tech guy and the marketing guy on the call have a modicum of understanding about how the conversation goes. (For example, not saying "we were hoping to get some coverage because we just signed an ad contract with you guys.") And finally, I know the agency will not contact me unless the company truly has something to say.
Because of these factors, I know that there's a high likelihood that engaging with the start-up will result in useful content for my readers.
In contrast, dealing with an unknown company and unknown PR person, it's a crapshoot. I can spend a bunch of time and have nothing to show for it.
So, when I'm under the gun (which is most of the time), I will always favor the interactions that are most likely to result in content I can use.