The Flathead engine can be a very maintanable, reliable and sturdy engine, I have built a few over the years, as far as overheating problems go, it's hit or miss...the problems lies in the way the blocks where cast, because these blocks where "sand cast" and the water jackets are small and in the block sometimes the water jackets are restricted and do not allow all parts of the motor to be cooled. The aftermarket for Flattys has exploded in past years and with more people building them it'd not as difficult to get good machine work as it used to be. Now for the mains if you are building a high power flatty "Flathead Jack" sells a billet main support system, and other main bearing supports, this is not really nessessary unless you are planning on building a stroker, or supercharging. also look for a "8BA" block to start with, that will put you ahead of the game to start with, also the are some "french military blocks" floating around that are superior in casting and construction that only require small amount of modification. Tranny swaps: the most common trannys to put behind a flathead are the C4 and s-10 T-5 there are a few other conversions out there but are expensive.
Well hope that helps, if you do decide to build it send me some pics, I've always had a soft spot for flatheads, (and rangers of course)