I checked my packing gland the other day, I haven't adjusted it for a while. It dripped about every minute when not running and every 11 seconds when the shaft is spinning. The drip has a path to the bilge. the bilge pump does it job. I'm not worried about it.
IF your handy. It would be worth hiring a good mechanic (they don't advertise, ask a sailor you trust for a reference) to repack your gland. While they are there have them service your diesel including changing both of your fuel filters, bleeding the air from your fuel system, changing the oil and filter, adjusting valves, changing impeller, anodes?, and checking anything specific to your make and model.
Offer to pay the mechanic extra to watch and ask questions. Take copious notes and start to evaluate how much you can actually do yourself, what special tools you need, and a list of urgent and recommended upgrades.
Buy your engine maintenance and service manuals. The more publishers the better. Have spare maintenance parts.
I have a 27 footer and am very handy. I used to work as a marine machinery mechanic on nuclear subs for the navy. I still paid a mechanic $500 to show me how to service my engine 15 years ago after I bought my boat. Expect to pay more today, a good mechanic should be taken care of.
If your not handy...
I told an old friend that you should be handy or have some money if your going to have a sailboat. He corrected me, "You better be handy AND have some money if you want to have a sailboat."