...like orange said...spend $20 and buy a compressoin gauge...compression will tell u tons about the motor. If each cylinder is 110 or better, the top end should be OK. I did a topend rebuild this past spring, and I, like you was a newbie to wrench'n, but was able to accomplish a topend rebuilt...new gaskets and rings. However, if I could go back I would not have replaced the rings...compression was OK on all but one cylinder, so that was $120 I could have probably saved. I had a bent valve in one cylinder, and that was the problem.
At any rate...if it ain't broke, don't fix it. If it runs good and its just an oil leak, just replace the gasket thats leaking.
You didn't mention how many miles it had on it. These mills are pretty durable...you can resonably get 30K out of the top end, and closer to 100K out of the bottom end.