Hard starting when hot is fairly common because the intake is in intimate contact with the exhaust manifold. An insulated spacer between the carb and intake can help. If your heat riser is stuck in the heat on (cold start) position it'll make the problem worse. As for the oil my guess would be the rocker shafts are upside down. The only way to verify or eliminate that possibility is to pull them and see. Yes the holes should be down. FWIW I have a bit of a problem with hot start as well although my '38 does start with a bit of cranking when hot. The heat vaporizes some of the gas in the float bowl which then fills the intake runners with excess vapor. You're, in effect, trying to start a hot engine with the choke on. On a hot day I plan my stops accordingly. I've considered making a simple heat shield out of some aluminum flashing to go between the carb and intake but haven't been that gung-ho yet.

Save a life, adopt a senior shelter pet.
The three main causes of blindness: Cataracts, Politics, Religion.
Name your dog Naked so you can walk Naked in the park.