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Re: Drawing circle from midpoint cause "Sketch could not be solved."
Your sketch could be as simple as this image or even simpler if you want to do the fillets on the solid model instead of in the sketch. the hole tool can be used to create a counter bore through both parts using the points as shown in this sketch. and the feature tree might look like the 2nd pic.

Re: How do I get the extrude remove to intersect with the surface?
Make your solid extrude part first, then Boolean subtract it from the surface part.
Re: How to remove center mark and tapped construction geometry
Right-click the view, then go to Show/hide then hide auto centermarks and hide threads.
Re: This type of error makes my experience of onshape incredibly frustrating
@martin_danger - I can't swear to this, but I suspect there are issues with (id's/naming) of faces or edges - and this is causing the feature to fail (and why it works in two separate operations). Fillets and chamfers are notorious for being touchy concerning order of appearance issues. That's why they recommend doing those operations last, if possible. This is not a terribly good explanation, but I hope it helps a little
Re: WTF happened ?????? We have to pay now??
Note that it is against the Onshape Terms of Use to use the Free version for commercial purposes.
https://www.onshape.com/en/legal/terms-of-use
Free versions of the Service are intended to support (a) creating and editing intellectual property for non-commercial purposes, and (b) viewing, commenting and import/export for commercial or non-commercial purposes (to the extent the plan offers those features). If you intend to use the Service outside a trial context to create and/or edit intellectual property for commercial purposes (including but not limited to developing designs that are intended to be commercialized and/or used in support of a commercial business), then you agree to upgrade to a paid subscription to the Service. Trial and free versions of the Service are otherwise subject to the terms of this Agreement.
Re: I need this like yesterday. Surface creation by 3d snap
With your Fill approach, quality is one thing (and yes it will be quite bad), but performance will likely be even more of a concern. With the boundary and the guide points, there is a lot going on in order to fit a surface. When things get so constrained, the underlying math gets more and more hectic…
Re: Intersect plane with mesh?
Yes, you can split the Mesh part (whether it is watertight or not) using a Plane. It maybe necessary to Enclose the the split part and plane(s)… Once you have a solid part you can, as @eric_pesty mentions, sketch on it and Use the edges.
Quick example: This mesh has been split into various sections. Note it is useful to have Highlight boundary edges turned ON. Better still, make a custom keyboard shortcut (mine is shift-6) to toggle in on and off :)
Now Enclose using this part and the two planes…
Sketch on that front (now analytical) surface…
… extrude it, whatever.
Or maybe shell the whole part…
Re: Is it possible to make a self-intersecting sweep?Who knows what tools can be used to do such work.
Do the sweep in sections that don't self intersect the section being created. and merge them together as you create them.

Re: Offset part axis to face
If you share your document, that would help the investigation. But, if I understand your goal, I think a slider mate with some offsets will get you there.