Hi Nate ~ I have built a Chester Yawl that has no bow eye or painter. For water use, I slip a line through the scuppered inwales. For moving the boat, I feel your pain, however I have a CLC boat cover that fits the CY pretty tightly and it has eyelet loops at the anchor points. What I do is: I have one ratchet strap that goes from the trailer frame over the oarlocks (I keep them in, so they keep the strap from sliding) and back to the frame on the other side. I do not overtighten, I also pass bungee cords through tthe cover loops and attach to trailer frame.Especially important, is the bow loop. I pass abungee and secure it to the front post of the trailer or the scicor and roller. I have trailered her many times over 8 hour drives at fast highway speeds and she stayed put with no damage, whatsoever. I all faireness, I have made 30" "sleeves" out of fake leather and thread the bungee through, so that no vibrations will afrade the hull paint. I also stick a microfiber cloth under each anchorpoint, between hull and cover. I baby that CY. On the other hand, I have a Skerry that is not finished nearly as cleanly and while I take good care of it, I do not go to the same extend. I have a beautiful cover for it that is not a tight fit, so I strap the boat across the oarlocks, which stay on. On the absence of bow eye, I put a cleat on the breasthook and I just cleat the bow to the front post. It prevents the bow from moving and has very little pressure. the strap across the oarlocks is what keep sthe boat on the trailer. Same thing: highway speeds not a problem. If I can post a picture link, I will.

Hopefully, this link with pictures works for you and illustrates better than my description, above:https://www.dropbox.com/sh/5bljthv8vf7ymim/AACdP86EG9m8lq3BnFWq32wJa?dl=0

   Does the painter come through the stem of the bow or is it in the breasthook?  On my skerry, I mounted a cleat on my breasthook to allow for dock lines, tie off an anchor line, etc.  It is also a good tie down for the bow on the trailer.  For something this light, I'm not relying on the bow tiedown except to keep the boat from moving backwards.  It's a piece of braided rope and a cam cleat on one end, going around the bow on either side of the stem, through the cleat, and down to the trailer tongue.  I use two tie down straps, one around the boat at the forward seat and around the trailer and a ratchet strap at the rear where the trailer tiedown brackets are located, to hold the boat down firmly on the roller and bunks so it doesn't bounce.  This is a Trailex trailer like in this photo from this site:

If your painter is removable, I might think about making a short painter with an eye splice, then splice a snap shackle or carabiner (locking!) to my painter extension so I could clip it on, or with it off, use the eye as a bow eye for the trailer.  Just a thought.

To clarify, I have a stainless 4" open base horn cleat on my breasthook, and a cam cleat on the end of the tiedown sort of like this.

   unfortunately my cover for my peapod comes with an ungodly amount of straps that in places awkardly attach to the trailer so I likley will not be doing that at the boat ramp before I pull her up.  Based on how busy it has been in late September- early October next summer is going to be a madhouse, and the faster I can get off the ramp itself the better it will be for everyone. 

The painter goes through a hole in the bow, and is removable (stopper knot on inside) but again, since I am using that to tie off while I fetch my car, I am not looking forward to untying it and threading a stubby one with an eye splice, but one possibility is a variation f that, put eye splice on the long one, and just choke up on it and put an additional stopper knot on it on inside solely for trailering.  Still would be a bit annoying on launching though, I would have to reach in there and untie the bight stopper.   Also, the way my existing trailer is there is not much space between the bow and where the hook for the strap goes. 
I have two other options, 1) tie off not at the hook of the trap, but the eyelet where the strap to the winch goes (back of the hook, as it were) and this eliminates problem of knot eating up precious space between bow and hook, but my concern is even this manual winch is way too much pulling power for such a light boat, and tightening it into the bow roller till the next cam click I suppose I could crack my hull.  As it is I just float the boat onto the trailer and guide it with one hand to the bow roller.
option 2) was going to be really sexy but I am stymied by the complet lack of "erector set" parts to make it work.  I bought a "skywinch" which is essentailly sort of a cam/crank thing, only for light boats.  you feed the line into the roller directly, no strap or anything, and crank away.  It is not as strong as the existing winch which is decidedly a good thing, and it's fast and easy and would play really nice with a painter.  BUT.  It uses a two hole bolt pattern, that my trailer does not acommodate, not can I seem to buy off the shelf parts to make it work.  Maddening.  I have thought of drilling two holes in the top of my winch post and just mounting it there (I may still do that) but that would compomise the galvanized nature of the trailer.   If I did that I would move the original winch/bow roller lower so as not to interfere.

Here is quick pic of my existing setup, 1.5" wide winch post on an E-Z Loader trailer.

https://www.dropbox.com/s/6fajtnovvmnes9q/IMG_1793.jpeg?dl=0