You should not worry too much about resale that is 5 years off. Trends change very quickly and what works for one house can look odd in another. I do not think your doors and cabinets are oak. That is not the usual look of oak - someone with better experience with wood will be able to tell you more. Warm wood tones are returning, so you can just leave the trim and paint walls in a pretty neutral. Creams, sage greens, green grays and whites tend to work better than cool grays with warm wood tones. A white with a gray undertone or greige may also work, but the greige would probably over do the brown tones in the space. If you can afford it, a natural or lightly stained oak solid hardwood floor would look good and fitting in the space. That is a more traditional floor, but since it is in homes over a hundred years old and still used today, it would be timeless rather than trendy and flexible to style changes. Your trim looks to me that it might be pine. I did paint my dark stained pine trim, but did not paint my cabinets and interior paneled doors. Wood interior paneled doors have more value than white, which are usually MDF. Wood moves with changes in temp and humidity which can cause hairline cracks in the paint at the joints. For this reason most factory painted cabinets are MDF or a wood and MDF comb. Wood doors are also much easier to care for than white. A painted over previously finished surface also does not have the durability of a factory painted finish - though paint can extend the life of worn cabinets. Here are some examples of white trim with wood doors. These pics also show traditional hardwood floors.:

I can't see any pics but would love to !! Sounds like I have a similar home and I am wanting to know what to do with all the wood too !!

I think the ceiling is more of an issue than anything else. If the drop ceiling could be reconfigured and painted to one color, and I think white would be good - I believe this would greatly enhance the space. I would leave all the wood. I would paint the painted areas around the bar, and any other painted walls, a warm white. I think I would use Benjamin Moore’s Ballet White or Swiss Coffee. And I like BM’s Natura Line. As far as the floor, since you are looking at LVP, I would personally go with a lighter wood look for flooring. Something like this.

Ok...now here's a lesson in 'light'. A dark floor SOAKS UP light (black holes are black because they suck the LIGHT out of the Universe...see where I'm going with this). You will need to involve someone with CAD who can do a design mock-up of your space. They can add in the windows and angle of the sun. Then they can add in the dark colour of the floor. The program should be able to 'soak up' the light to show how dim the space will appear. Then they can add in spot lights in the ceiling. Each spot light will have a ring of light which it sheds. The ideal amount would be to have every pot light 'ring' intersect with the NEXT ring. You will do this for every square foot of your main living space. Which means you will need your electrician to update your panel. You will need 'almost double' the lighting budget and add in a snick more for electrical work. OR... You can go with a MID-TONE floor (same colour range) and leave everything as it is. A mid-tone floor DARKENS in a space. It will offer all the drama of the dark floor (even the appearance of being dark) without ALL the down falls. Find a colour that is right (that works for you) that is also 3 STEPS lighter than your current choice. It will get DARKER once installed. I promise.