Hard to me to say since I'm only 5'11" but the V-Berth length is about 75". Diagonally this distance is a little more. So, I would say you could fit but it wouldn't be super comfortable. Headroom is certainly less than 6'4". Not sure what it is but maybe 6'2"? However, the headroom is fairly consistent throughout the house length. So, there are definitely more comfortable boats for a man of your size in these terms but to me there are more important considerations such as overall quality of construction, layout, seaworthiness, and overall value. I would consider carefully what you consider to be your top requirements. The T37 offers a lot of positives for an old production boat. What I have come to appreciate is the construction quality (although I am dealing with deck core issues that should be expected with balsa), the seaworthiness, and the keel/CB arrangement for cruising on the Chesapeake. The boat has excellent sail carrying capability (i.e. stability) for a keel/CB. Sailing upwind it carries a bit of helm as is typical of designs with fine ends, but steering is predictable and the boat tracks well. My GPS tracks in full power conditions show that the boat tacks in a bit over 90 degrees with leeway which is not terrible for a k/CB. The overall performance is decent and it will handle a seaway pretty well although pitching moment is a bit high. The cockpit is well-protected. And, for value, it seems that you can get an exceptionally well-equipped and well cared for T37 for around $50K. Conversely, if boat work is your thing, you can also get a "beater" that will soak all your time and money for very little. Personally, my T37 was in the family so it was an easy decision to begin a long and costly refit. I'd be lying if I said this was the boat I really wanted that was within reach (I plan on eventually moving to a J42), but it has turned out to be pleasantly surprising in many ways (and annoyingly frustrating in others). As for weaknesses, certainly this is not a modern design that offers lots of interior volume. Most T37s are also quite old now so every boat will have issues, most of which are well documented here. The good news is that if you do buy one there's some great knowledge here on this forum to help. A bit more info than you asked for but headroom is really just one consideration.
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