How handy are you Nicole, or do you have the budget to hire someone to replace your trim? That would be ideal. Choose a paint-grade moulding and prime and paint it before it's cut and applied to the wall. Then you'll only have to touch up the nail holes and give a final coat. Much easier than painting your existing trim, and much more interesting, because you can get some very nice profiles of mouldings.

But if budget is an issue, and you have time and ambition, then you can prime and paint your existing moulding. Either way, you will certainly have an up-dated look and you no longer will have to incorporate the oak colour into your colour scheme and decor.

Thanks for your advice! Do you think I should go white then?

Absolutely with no doubt for sure yes please do! LOL

Some of the base board trims need to be replaced, but the trim around the windows and doors could just be painted? Think it's better to get someone to do this for me? I could possibly do it?? What kind of white paint do you think is best for this task?

This is your opportunity to upgrade the trim so I recommend you go with wider baseboards, six inches at least (in height). Then you can select a similar profile in a wider and door trim, maybe 3-1/2"?? When I look at the photo of your triple window I see a tiny sliver of wall between the trims. You could size this so that there is no gap and the trim colour will surround the window as well as beween the windows.

If you set up a work station with saw horses or a couple of tables, you could do the prep work (priming and painting). Then you could have someone come in with a good mitre saw and a nailgun with a compressor and zap zap it's done beautifully. If you have to nail by hand it will take forever and you're bound to miss a few times and dent the trim.

As far as paint is concerned, it can be in a pearl or satin finish (Benjamin Moore). Other manufacturers have different names for their sheens. Somewhere between an eggshell and a semigloss is what I prefer, hence pearl or satin.

I always use Ben Moore semi-gloss on the trim. It is a nice contrast to an eggshell finish on the walls. It is a lot of work to paint over wood stain, sanding, primer coat, sanding and 2 coats of finish paint, so I would suggest getting a professional to do it for you, well worth the money spent.