My thinking on any remote drain method is that it's another system to fail. I would sooner cut an access hole in the plate. If the hole leaves something vulnerable, then being steel, tag a flange around the top opening of the hole to bolt a cover plate back into. Flathead socket heads are easy, but they too are vulnerable to stripping & trail damage of the hex socket.
My preference is to use hex head bolts sunken into fabricated counterbores. First make the filler plate. Put holes in it big enough for the socket for the plate holding bolts to fit thru. Then make spacers roughly the thickness of the bolt head minus the thickness of the plate, if needed to get the bolt heads flush to below flush with the bottom of the plate. Next make the plates with the bolt holes. Weld this all together and then make the flange & spacer(s) on the skidplate. Rarely do I go to that much trouble.
If that's simply not an option then I'd consider some sort of remote drain method. The very first thing I would do is figure out what the thread size & pitch of the drain plug is. Then dig into the various fitting catalogs looking for an adapter fitting to that thread from one of the AN/JIC dash sizes. Preferably you've find one in a steel (JIC) fitting instead of an AN (aluminum). There are a lot of adapter fittings that use a crush washer seal. Also, nearly every fitting design uses a std bolt pitch & size for it's threads i.e. the -6 JIC/AN 37* fitting uses a 9/16" NF thread, as does the -6 O-Ring Boss (ORB) fitting. There are metric crush washer std fittings and the odds are reasonable that you can find an adapter fitting to work. When necessary at work I have been known to use a large size NPT fitting and turn it down to make my own metric crush washer adapter.
Once you have that, then you can pick the valve and it's mount location. The way I did the drain on the dry sump tank on work's Turbo Test stand was to use a regular ball valve combined with a couple JIC fittings. I used an NPT to JIC/AN adapter
out of the valve, and then put a JIC Cap on the fitting. This way even if the valve's lever does get moved by something/someone w/o first removing the cap the oil still can't accidentally be drained.
I would use rubber lined braided stainless hose for the connection. I wouldn't use the more spendy teflon lined hose b/c it has a tendency to kink & possibly rupture when crimped. I would choose the braided over the other options for it's effectively being armored. A very good second choice would be the hose used in OTR/Class 8 truck oil systems (Weatherhead HO69 or equivelent).
For a remoted oil filter I would not buy one of the kits. I've yet to see one that had the correct hose & fittings for the job. Frequently the remote filter pad is one of the cheap, cheesy die castings. There are good die cast & sand cast filter pads out there, just need to look for them. The problem with the cheep ones is that they usually do not have enough strength btwn the mounting flange and the filter's flange. A full oil filter isn't light and I've seen quite a few of the cheezy ones fail at the desert races. There are billet pads available. They're spendy, but usually do not suffer from strength issues.
System One (p/n's 222-90007/8)and
Peterson Fluid Systems both make nice parts.
The kits usually come with cheep hose and multi-barbed fittings that use hose clamps. There is a reason race vehicles don't use hose clamps on thier oil system plumbing & given where such a thing is likely to fail for anyone on this forum we shouldn't either. A reasonable cost option is to use the so-called "Push-Loc" or "Barb-tite" fittings and their specific hose. My hose of choice for this type of fitting is Aeroquip FC-332. Oil, gasoline, and diesel have no effect on either the inside or the outside of this hose. The fittings have 2 or 3 barbs, depending on size, and you will
work to get the hose over the barbs (use oil on the fitting & the ID of the hose), however if you leave a little extra length any problem with the hose at the fitting can be field repaired. These fittings
do not need nor want a hose clamp. Using one will cut the hose on the barb. If that makes you a little nervous what I do in locations where others need re-assurence that the hose won't come off the fitting is to either put a tie-wrap/zip-tie between the first and second barbs, or do a double Safety Wire wrap in the same place. These need only be snug, not tight. Tight invites the same cutting problem.
Well now, that went longer than I thought it would.....
apprapo that it's my 100th post here.