It's all about the appropriate tools matched to the appropriate skills matched to those slippery terms 'taste', 'authenticity' etc. . Agree that spacing, flow, alignment etc are matters of eye, judgement and skill. But that CAN be done on a computer...by someone who's got an eye for spacing, flow, alignment etc. and the skills to use the software to adjust accordingly.
To answer the OP, I actually (heresy, heresy!) used good old fashioned Powerpoint to design our boat-name, and have often used it to design other stuff before, if necessary, moving on to Photoshop or Illustrator if I need more complex work doing. Powerpoint is pretty basic (but not THAT basic), and with some skills etc. can be used to create interesting and quite complex designs.
I really can't accept the vinyl lettering = bad, hand painted letter = good argument. Both can be good, both can be execrable. Give me well designed and executed vinyl over badly designed and executed hand painted lettering any day (and vice versa!).
Going all intellectual for a moment.......Walter Benjamin identified the problem way back in the 1920's when he wrote his famous essay: 'The Work of Art in the Age of Mechanical Reproduction'. What is being discussed here, Benjamin calls the 'aura' of the original. And people do value the 'aura' of an object, and the 'aura' comes from its uniqueness and the manner in which it was fashioned. Which is why people will queue for hours to see the Mona Lisa behind its inches-thick bullet-proof glass rather than gaze on it on their tea-towel or mug in the privacy of their homes.
So the unique, hand-painted boat-name will always have (for those who know it) a special 'aura', that vinyl, no matter how beautifully crafted, will never have....but see below...
...and on a similar note.....We live in a road of Edwardian houses. Architecturally almost identical. Lots of wooden bay windows and oriel windows, lots of leaded and stained glass. It's a friendly, pretty stable, quite close-knit community, and most of us care about our houses, keeping the period 'feel', and maintaining the 'visual environment' (sounds familiar?). So, though nothing is ever said and no criticism made (now that DOESN'T sound familiar ), like is generally replaced with -usually expensive - like So when a long-standing neighbour decided to replace all their windows we were horrified to see the uPVC window installers arrive in their big glossy white vans covered in vinyl lettering. But a strange thing has occured. Yes they've used uPVC, but the end result is excellent!! They've kept all the proportions, details, stained glass etc of the original (but now rotting) windows. You have to actually go up and touch them to get that 'I can't believe it's not wood' sensation.
So...uPVC v. Wood, Vinyl v. Hand-lettering. Hand Craft s v. Technology, Sustainability versus Non-sustainability..... choices, choices.....
(edited for typos)