Na, 'kerl...
If you take your time and work in relatively small areas, you can go back and brush out the tide marks around oil washes as the wash is "setting" (in that in-between stage between wet and dry).
This is a major advantage to using oils over acrylics - the increased working time. However, you will need to slow down and take a patient approach to the work. If you work in an area too large, the tide marks can form and dry before you get to them. How big an area to work in depends on your own speed and style. I tend to apply washes and CM to fairly small and distinctive areas, but I work pretty slowly.
Something that will help is Iain's advice to pre-wet the working area with clean thinners before applying the wash. However, you still need to look out for hte tide marks as they start to form. Pre-wetting won't completely prevent tide marks from forming since they form because of capillary action.
A clean, slightly dampened brush worked around the edges of the tides as they form will eliminate them if you're using oils.
Be sure to clean the brush off as you work out the tide marks. It will pick up extra pigment and binders from the tide areas, and if you don't clean it every now and again, it will transfer those to other areas.
I work pretty much exclusively over flat-finished areas and only gloss clear coat for decals, so in regards to your question about whether it's best to apply your washes over gloss or flat, I'd say you can do so over either.
As Mathew says, the flat finish tends to "grab" the pigment and hold it in the area where it's been applied (the major exception are the tide marks). This is an advantage to flat finishes, though. You can get the colors to stay where you want them. This is where pre-wetting can really help by increasing the flow and spread of the wash over a flat finish. My guess is that over gloss finishes, the tide marks wipe off easier since the pigments are not down into the finish like with flat coats.
Also, pre-wetting helps to prevent oil-dot color modulation from "sticking" too quiclky to a flat finish and makes it easier to blend out.
Much of this is individually technique and style dependent. Different modelers can can use different techniques, materials and finishing styles to achieve essentially the same final results, so in the end, you have to find those techniques that work best for you and develope your own finishing style.