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why would oil type/brand matter?

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Because in my past experience of using Quaker State oil I had a similar problem and I switched brands and I never had the problem again. I was curious to see what brand he used.

I used shell rotella oil.Today I looked at the pcv valve.The previous owner had tje vacuum lined reduced down to a pencil size vacuum line and plumbed into a very small port at the front of the carb.This port was below the throttle blades so it probably wasnt full manifold vacuum but I didnt check.I ran the line to the rear of the carb where it belongs.Hopefully that helps.P.S. we have been driving it to work-25 miles one way.

You can install a warmer thermostat to help too.
My small block was happier with a 195 than a 160...

I saw the same thing this morning when I checked the oil on my 440. I ended up canceling my day of cruising because I didn't want to risk running it without doing a compression check. We live in Hawaii and don't see temps below 70 in the day that often. So all my buddies here are freaking out because we don't see that too often. However, we recently moved to the much higher central Oahu where its always 10-15 degrees cooler than the rest of the island. At night and early morning the temps get down to low 50s. I know its only 10-15 degrees but the humidity never leaves 80-90%. So I guess this makes sense. The car hasn't seen temps this "cold" since its been on island.

I probably just pissed a lot of people off, talking about how "cold" it gets on Oahu.... my bad. Hey at least most of you mainland guys have a track to run on.

I can't believe this.
My God it is that time of the year. Even in Hawaii you are going to have a certain amount of condensation. There is even condensation in the desert to a certain degree. It is a natural combustion byproduct in an internal combustion engine.
Yesterday there was an actual ice build up from one stop light to the next from water running running out of the exhaust at -20 degrees. I have an ice build up on the quarter panel of the truck from a hundred and twenty mile trip in that weather.
You won't find anything wrong other than short drives not burning off the condensation. Blown head gaskets are not that common. Coolant leaks do happen periodically but a great majority are external when they do happen. The colder the weather the longer it takes. Just because the temp gauge reads normal don't mean that the engine is completely warm or for long enough.

I want to put in an oil temp guage but I'm not sure which temp range to get. There are some that peak at 180 degrees and some that start at 180. What do you think?

My problem turned out to be the pcv valve not hooked corectly by a previous owner.All is fine after plumbing it into the proper place and changing out the plugged valve cover breather.No motor condensation on the dipstick tube.Thanks to all the people with useful suggestions.