You just have to have confidence you can do it and then do it. I had someone come up and do the first service (my first tractor) and I watched it all. After that I had the confidence I could handle it. One point: at that first service the guy could not get one of the hydraulic filters off - he tried everything. After an hour he was going to give up. I suggested we put the vice grip oil filter wrench on the filter, hook a small chain to that and to my pick up and let me try to nudge it off that way. He said no, he tried some more, than said we would try the pick-up plan. It worked - popped the filter loose.
A few points:
-- it sure is convenient if you have one of those mechanic's creepers to get under the tractor- especially if you are 72 like me.
-- when you put the filters back on spread some new oil around the rubber gasket - that way they will come off easier the next time.
-- read the manual carefully so you don't miss anything - I prepared a check list for each task. There can be a lot of plugs to drain- for the hydraulic fluid, the engine oil, the front axle, and perhaps more - I think there were 9 or 10 I had to access. Also learn about all the lube points on the tractor and FEL or whatever.
-- make sure you have all the correct filters for oil and air, and enough oil, grease, etc. before you begin.
-- if you have a sight glass it would be useful to add dye to the hydraulic oil when you refill it.
-- have sufficient containers to collect the old oil for recycling.
-- have a lot of rags.
-- If you have questions, remember you have access to hundreds of skilled tractor guys on this forum.
-- It will be much easier the second time.
-- after you are done, write down anything that was confusing or unique or that you might need to remember the next time.
I consider that I am a bit of a newbie - certainly a novice at maintenance. Less than 900 hours on the tractor. It will be very satisfying once you do this, and you will learn a lot about your tractor.
NOTE: my tractor is a Kubota 3410 - I don't know much about Bobcats but hopefully some of these points will be relevant.