Never did liked the DB9 DB25 connectors, even as solid they were back then. The only way to really secure them meant screwing the two screws to the sides - otherwise these made for poor quick securing connecting and disconnecting. This goes as well for the VGA connector too. However, I never had a problem NOT screwing in these connectors.
Also, with USB, HDMI, and Displayport connectors, they go in fine. A rule of thumb for me is that I shouldn't force a connector in to have it work, the connector should go in smoothly. With the three mentioned connectors, I can eventually blind connect them.
Looking when connecting, the label should be facing up. (with motherboard orientation and device orientation though, this is getting ambiguous - tower PC setups have the USB label facing up away from the motherboard and on the fan heatsink side).
What sucks is that Micro USB requires some force and it isn't as smooth. Mainly due to the two prongs needed to secure the tiny connection in place. They also need some tiny force to disconnect due to that factor. But Micro USB does the job in a compact USB connection... Being tiny, there is risk in blindly figuring out the connection - moreso than normal USB (at least I have a good job in blindly connecting USB plugs).