I'm pretty much with "aeroncast65t" and his suggestions. Fitting a six is a rather drastic change of character for the car that might make it (arguably) a better highway cruiser but will take away some of the nimbleness of the car as it is now (think Spitfire / GT6 corollary here).
With almost any engine upgrade (or swap), I feel that the front disc brake upgrade is a good idea. Nothing against the original front drums, which to me are just fine for 40- or 50-hp 1200 Heralds, but anything more than that pretty much begs for front discs and the corresponding master cylinder (with its larger reservoir being the KEY difference). Yes, a dual-circuit brake system is good, but I've yet to have an instant/catastrophic failure of a single-circuit brake system short of bursting a hose or steel line. Funny thing is, such an incident seems almost as bad on a dual-circuit system; remember that maintaining your "handbrake" is nearly as good a safety measure.
Although I'm mostly a purist, I do respect (and occasionally consider myself) "period" upgrades. In this case, a Spitfire 1147cc engine, or at least the camshaft, head, carb/manifold and distributor from one on your rebuilt short block, is a great (and essentially "correct") upgrade. The earlier 1296 is nice as well, but I always liked the 1147 just a wee bit better. Either way, an OD gearbox is a nice improvement for higher-speed cruising, too!
Getting back to the chassis, ensure all the bushings and such are sound, then toss in a set of Konis and maybe a camber compensator (or "proper" swing-spring kit, not just an old, discarded Spitfire swing spring), and enjoy!