Only go in-house if you are handling lots of files and doing lots of operations. And also, if you're looking to scale. But do have in mind that you're gonna need an investment.

So, always go third party, specially in 1.0. It's simple.

Take a look at this project if you're thinking in in-house in the future: github.com/thumbor/thumbor

CDN is not a better solution.I think third party is best compare with CDN.

There is no need to re-invent the wheel, unless there is a constraint.

I think at initial stage it's good to try third party bkz there are lot of stuff in need to be done and a team alone can't lot much time on developing on stuff. You can roll-out this plan and this in your roadmap for next quarter with low priorities .

I will always go for self hosted first.

Only if the projects scales I will consider a third party. Having a dedicated static server is not rocket science nor is it high maintenance.

If we scale we can switch to a third party. However if the projects aims to be big and it has it's target audience across the globe, I will go for a CDN or the cloud.

Bootstrap businesses with little to no budget? Cloud-based 3rd party services are the savior.

Venture-based businesses with seed capital to flex? It might be possible to discuss a CDN, depending on the necessity and scale of the media bandwidth.

I would go for Trusted third party. Building for 1.0 is really hectic since you do not already have the exact road-map, it is always better to go with Third party CDN (eg: cloudinary.. etc). This would reduce a responsibility on In house team and would give more room to try new features instead of building infra for images and other CDN. This would cost extra bucks.

It depends on many things, economy, time, use case, etc.