Engine What to do now?

Gents, so far this site has been in valuable to getting my 1990 convertible back to full operational condition. Of course you always want more! I am taking off for work, for 90 days, that is a lot of savings for when I return. Now what? The car is at 105,000 miles and runs great! Everything works including the ice cold air! I do have a decent oil leak, assuming it is from the rear main? My valve cover gaskets are the rubber/metal SVE models and they are a few months old and dry. My oil pan has been dropped slightly in order to facilitate a new front cover replacement and bolts re torqued. No wetness around the circumference of the pan except around the rear main? If I drive it and let her sit overnight there is about a 1/4oz sized puddle on the floor.
Here is my conundrum, when i return I plan to install some aluminum heads (AFR or TFS) and a lightly ported explorer intake. Now I am thinking maybe if i am going that far I should pull the whole thing and do the rear main and replace the oil pan gasket with a whole unit? Maybe freshen the bottom end, new rings, bearings, and put in a custom grind in to get the most out of heads and intake.
Here is what is done to it- factory gears, when i return the entire rear will get refreshed with 3:55 gears, it has BBK 1 5/8 shorties, BBK catted X pipe and flowmaster American Thunder, BBK 65mm TB, 75mm MAF, fender well cold air, non EGR explorer intake, I have a ported internal EGR intake almost ready to go, just have to port the lower to whatever heads I get, new FMS timing chain, new water pump, SVE radiator, 3G alt, and a rebuilt air pump. Everything works except with the non EGR intake the EGR is currently in op. I want everything working properly.
What I want - I want this car as a cruiser, it is pretty cool. I drive it 50 miles a day 3-4 days a week. I want to stay NA as well as be able to idle in traffic with the air on in the 90 degree FL heat and finally be able to scorch the tires on command. I would be fine not touching the cam and going with 1.7 rr if the drivability will be an issue but I am assuming a custom grind and subsequent tune can smooth out drivability issues?

What would you guys do?
 

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