The Irwin 37 CC was designed as a cutter rig. The head stay on your boat is in the correct place, however your current roller furler even though is ib the right place on deck does not belong at the top of the mast but further down where it would be parallel to the head stay. You can find drawings by googling Irwin 37 CC.
Look at your must about 5' down and you might find an attachment point. It might have been removed or ground off or maybe even if you're lucky it is still there. You will find then that the sail luff will be long enough. Next you need to buy a head sail with a high cut 'Yankee'.
Cayennita is correct.
First some 'teminology' for a cutter rig:
• The front stay is the HEADstay onto which you attach the jib or genoa .... (or 'yankee' - a high clew sail used for heavy weather sailing.)
• The second sail back from the front or 'head'sail is called the
FORESTAYSAIL ... shortened to 'staysail' or stays'l ... and the staysail/stays'l/
forestaysail is flown on the FORESTAY, the second stay back from the bow ... or the stay thats a'
fore the mast.
The HEADstay should be parallel to the FOREstay .... so your rig has either been altered or the current configuration is in error. The forestay should connect a few feet lower from the mast head ... and as Cayennita has stated there should be or 'was' mast hardware to attach the FORESTAY there well below the mast top.
If the current mainsail is to the OEM designers specs./drawings, when the mainsail has been reefed to the 'first' reef position, the top of the mainsail should be more-or-less equal in height to the forestay—to—mast connection on the front of the mast.
Also on many cutter rigged boats of this era there should also be 'intermediate stays' that run from the aft most chainplate (and share the same chainplate with the aft-lower shroud/stay) and should terminate AT near the same posiition of the forestay connection (called 'hounds').
Cutter rigs can be a royal PITA rig to sail until you learn the 'intricacies' of such a rig. So until you learn such 'intricacies' and to 'sharpen your learning-curve' I would suggest that you disconnect the forestay and staysail, store the forestay 'in place' (tie or secure the forestay to the mast - but dont 'kink' the wire) ..... and sail the boat like a sloop !!!!!! Then when you are 'satisfied' with the performance, then reconnect the forestay and staysail.
The 'problem' with cutter rigged boats is that the TWO 'front' stays (headstay and Forestay) react with a
single backstay and under differing wind wave conditions you will have variable stretch/tension in the two 'front' stays ... and typically the longer 'headstay' will be more 'slack' than the forestay --- NOT good!. A slack headstay will interfere with or
lessen the
'pointing ability', will promote excess heeling and the boat will tend to 'skid to leeward' instead of going 'straight' when beating.
Hint: When sailing, especially when beating and with main/stays'l/genoa flying, the Headstay should always be 'tighter' than the Forestay ... and unless sailing in 'heavy weather' (when the jib/genoa is normally 'doused' & flying only the stays'l + main) the forestay should be fairly 'slack' (about 7-10% tension if you use a rig tension gage; the headstay near 15+%). The forestay tension should be increased when flying 'only' the staysail and with the headsail 'doused'/furled.
Suggest you sail the boat 'like a sloop' (Genoa/Main only) until you are well used to the boat. You can at any time attach the forestay/stays'l when you are reefed. This will save a lot of 'pain', especially in 'light' winds when the genoa/jib has to pass
between the headstay and forestay when tacking .... as usually the jib/genoa tends to get fouled when trying to pass between the headstay and forestay when sailing in light winds.
A 'true' cutter will have the mast at 50% LOD (length on deck) distance back from the bow; a sloop will have its mast about 30% back from the bow, an Irwin 37 will have its mast somewhere between, so you can easily sail the Irwin37 .... just like a 'sloop' and still get 'good helm balance'.
Hints on sailing a 'cutter rig':
http://www.arvelgentry.com/magaz/The_Double_Head_Rig.pdf