[Freakylabs4]

I have seen this molecule with the R-stereodescriptor on the C-Atom, that binds to the hydroxy-group, but every time I do this myself I get the S-descriptor. I've used ChemDraw and got the R-descriptor, but when I use the CIP rules then I assign the highest priority to the oxygen, the second highest to the C-Br and third highest to the ethyl-group.

[Babcock_Hall]

In the drawing that you provided, does the lowest priority group exist in front of the plane of the screen or in back of plane?

[Freakylabs4]

As it's drawn (or not drawn), it's in the front. I was told, that if it's not drawn into the structure, but another atom/group (in this case the hydroxy-group) is for example in the back (dash), it must by default then be in the front.
The structure though is as given in the picture I provided.

[Babcock_Hall]

To assign a configuration as R or S, the lowest priority group, which is "H" in this situation, must be in the back.  My preferred ways to do this is to rotate the molecule on paper or make a model and rotate that, but there are other ways.  What method are you using?