Removing as much hardware as possible will be a key factor in the longevity of your paint job. Hardware left in place, including the toe rail, is where the breakdown of your coating will start; on the edges. If you use a two part paint the hardware will also be an impediment to doing the job as the paint dries extremely quickly, leaving little time for 'cutting in' deck fittings. This is one of the reasons that some elect to use a single part paint, accepting it's shorter lifespan.
I would not be concerned with warping of the toe rail, unless you're the type to start a project and then forget about it for a year or so.
I would approach the project as a major one, allowing time for removal and rebedding of all deck hardware. While you do not state the age of your boat, all boats will need their hardware rebedded at some point in time. There can be no better time for a thoroughly done job of this than prior to the painting of the deck.
In the meantime, I would avoid any quick fix paint jobs designed to improve the appearance of your deck. Many's the restorer who has lamented the fact that, had nothing half-way been done previously, the job of re-finishing would have been much easier. Sail the boat as is until you are ready to do the job right. Bear in mind that most are envious that you are sailing while they do not even own a boat, much less even a project boat. It is quite amazing how little deck appearance effects sailing performance.(g) You'll have enough off water time when you decide to do the job to not want to extend the project longer than necessary.
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