Putting re-encoding quality loss aside, both will result in the same scaling quality -- when it comes down to the actual information at hand, you're taking a 1440x900 image and giving youtube a 1920x1080 image. It doesn't matter where in the chain this occurs from a resolution standpoint. There may be the question of which algorithm works best, and that may be something you prefer either OBS's options over Vegas or vice versa, but that's it there.
From an encoding standpoint, technically the best way to do things is to have the least amount of re-encoding possible. That would mean just having a straight shot from OBS to output. Any re-encode of a video file will always be a lower quality, even if you're putting more bitrate into it (you can't just add quality back this way).
That said, at the end you're also going to be limited by youtube and whatever re-encoding it does on its end. You could give it a perfect uncompressed exact video, and you'll still have to deal with the encoding settings of youtube's processing. The main difference here is youtube has 2 different encoders it can use: AVC and VP9. AVC is basically another name for h.264, and is going to be much lower quality than the VP9 encoder... unfortunately, for normal uploads it is unlikely to get the VP9 encoding at 1080p...… but if you upscale all the way to 1440p, then it is much more likely to get the VP9 encoder, resulting in better quality for the 1080p version on youtube.
Basically what I'm getting at is, it doesn't really matter where you do your upscaling -- it's not going to be noticeable at all compared to the bigger problem which is the re-encoding chain, with youtube being the biggest factor.
How I would do it personally is output a 1440x900 high-quality recording from OBS as a master, then create an upscaled 2560x1440 version with Vegas for youtube (which can then be discarded after upload). That way you have a high quality original resolution file for the future if needed, and you get the best quality that youtube can provide (hopefully).
If you don't care about keeping a master copy, then you could just output your final resolution directly from OBS, upload that to youtube, and call it a day.