I don't think it LOOKS amateur.
But, I also don't think people fully grasp what they give up when they outsource. Don't get me wrong, partially or fully outsourcing your infrastructure is not inherently wrong.
Basically, outsourcing is about removing the number of hands you control over your infrastructure, and to some degree, your business model (some online apps constrain you into their way of working). Yes, less hands means less direct expense, and that is the limit of the ability to think of some. Because they don't see the indirect expense of managing the managers, or the bigger potential expense that is taken on as risk.
I had a buddy have his data center go bankrupt and close shop, which not only took him offline, but also made him lose access to his colo'ed boxes for days. (BTW, his backup server was also in the colo. Ugh.) I have seen downtimes on virutal hosters cause another to almost go bankrupt for being down two days, which was a critical length of time to his business. I've seen a third company not be able to receive email from their 800 vendor contacts because their email provider implemented an aggressive spam policy that they did not want to roll back. They survived, but their reputation was dinged. Myself, in an older effort, I had used a backup service for keeping offsite backups of all my company servers. What didn't register was that the center was in New Orleans. Yep, Hurricane Katrina took care of that.
Amazon virtual servers (and like) are not cheap at all anymore, and severely underperform dollar-for-dollar. For the few hundreds a month you pay Amazon per server, you could get a colo box, fat bandwidth and get a sysadmin to help with the setup and occasional maintenance issue. You get to keep your data and your destiny.
OTOH, a law office I know waited two days for technicians to swap a motherboard on their in-house server. Yes, horrors exist on either side. That is why my strategy is to always use both redundantly.
What would look amateur (to me, as an investor) is someone who doesn't understand the pros and cons of outsourcing and has one-sided opinion of it either way.