Based upon putting over 2000 hours on Roam (2008 R-25 with Yanmar 110 HP) and performing most of the maintenance myself or with help from friends (Thank you Mike!), here are my suggestions.
Do whatever your engine manufacturer requires based on age and engine hours (oil, oil filter, fuel filters, air filter, impeller, coolant, anode, belt, mixing elbow, injectors, heat exchangers, transmission fluid, etc.)
Check and/or replace the thruster, prop and trim tab anodes (zincs).
Wiggle the prop and the rudder to check for play. Roam has no issues with this after 10 years. Give the rudder post one or two shots annually of grease. Marine Hardware uses a marine grease containing PTFE.
Lubricate the door lock, latch and hinges.
Spray the bimini with Scotchguard or something similar.
Check the steering fluid level. Inspect for leaks at the hydraulic connections for the autopilot pump, steering actuator, trim tab pump and the trim tab actuators.
Clean the sideways drain passages from the aft sides into the thruster and depth sounder transducer compartments. Also clean the passages that drain forward from the thruster and depth sounder transducer compartments into the bilge.
Remove and clean the aft bilge pump check valve (located in the hose near the holding tank). If this part is more than 5 years old, I would replace it.
Test the bilge pumps. Use both the switches on the DC panel as well as touching the embossed circles on the sensors. It's necessary to do this both ways as these are separately wired and fused circuits.
Remove and clean the cockpit drain screens. Do this much more frequently than once a year.
Tighten the nuts on the top of each engine mount. This requires a big wrench.
Inspect all of the hoses for chafe, wear, cracks and bulges. Replace as necessary. Check the tightness of the hose clamps. Be sure to check the heater hose clamps under the sink in the head where they attach to the water heater. These joints are difficult to access, but a common source of coolant leaks.
Remove, clean and tighten all of the battery connections and the connections of the grounding cables to the engine and the positive cable to the starter motor. I spray on a little Corrosion Block.
If you have lead-acid batteries, check the fluid levels in each cell and top off with distilled water as necessary. This needs to be done every few months.
Check the shore power cord and the contacts where the shore power cord is installed. Look for signs of corrosion, heat or arcing. Some tug owners have installed Smartplug systems, but I have not. This is discussed on other forums on this website.
Inspect for loose screws and other fasteners.
Inspect the wiring for chafe.
Check the windlass foot switches and replace if the membrane is cracked.
Spray Corrosion Block on the contacts for the trailering wire harness in the anchor locker.
Clean the anchor locker and rode. Make sure that the drain is not obstructed. Make sure that the seizing wire on the anchor shackle is intact.
Check to make sure the shift cable does not bind and is properly adjusted. If it binds or feels sticky, replace it.
If the head joker valve is original, it should be replaced. It depends on usage, but mine have lasted about five years each.
Check to assure that the straps that hold down the holding tank and batteries are tight.
If you have a Wallas stove, replace the fuel in the tank if it's over a year old. There is conflicting information about whether to use diesel or kerosene. Diesel is cheaper and more readily available. I believe that kerosene is cleaner and have been using it exclusively for several years without issue.
Your CO detector expires after 5 years. Replace if necessary. Some new ones last 7 years. There should be a button to test the alarm.
Check the running lights.
Check the horn. If necessary, there is a procedure for cleaning the horn contacts on this website. The horn sound will change before it fails entirely.
Check and clean the windshield wiper blades. Replace as necessary. Lube the arm hinges with WD-40 or similar.
Clean the window and screen sliding tracks. Diamond Seaglaze recommends lubing with silicone spray.
Turn your fire extinguisher upside-down and shake it. Make sure the pressure gauge is in the green range.
Inspect your flares and replace them if expired.
Adjust the prop shaft packing nut if it leaks while not moving or more than a few drops per minute while underway. If these adjustments become too frequent, replace the packing. In my case, the original material lasted 1500 hours.
Some manuals recommend checking the prop shaft alignment from time to time. In my experience, it doesn't change much after the initial 50-100 hours of settling of the engine mounts. If you decide to do this, it should be done while the boat is in the water.
Clean and check the operation of the shower sump pump. I highly recommend installing a switch that allows this to be disabled when not in use. If the float switch sticks, you could drain and destroy your house batteries, even with the master switch off.
Check the swim platform support brackets and fasteners for corrosion.
Inspect the trailering light gaskets. Replacement parts aren't readily available, so use marine silicone to seal if necessary.
Some people will insist that before applying anti-fouling paint, it is necessary to apply an epoxy barrier coat to prevent osmosis (blistering). I've been told that Fluid Motion uses a type of resin in their hulls that makes this unnecessary. Roam does not have an epoxy barrier coat and does not exhibit osmosis after 10 years. Nor am I aware of any Ranger Tugs or Cutwaters with osmosis.
Paint the bottom with anti-fouling paint or touch up as necessary. Roam is kept in the fresh water Great Lakes in the summer and Florida salt water during the winter. I've managed four years between full paint jobs if I touch it up regularly. I use Pettit Hydrocoat (Water based and $149/gallon at West Marine; often on sale, cheaper elsewhere). Follow the instructions to the letter. Use the specified wiping solvent. Three coats at the waterline, two coats elsewhere. Two gallons will do the job on an R-25 with a half gallon left over for touch ups. Other brands are popular in different environments. Ask around to find out what works in your area. I do get some smearing/wiping off in the first area of contact with my trailer bunks when driving the boat on and off the trailer.
There have been discussions on this website of anti-fouling coatings such as Propspeed to protect the propeller, rudder and trim tabs. I have not done this. I find that frequent usage and occasional cleanings makes the growth manageable in my particular case. If this were to become a problem, I would consider trying Propspeed or a similar product.
Buff and wax the hull and eyebrows. There are lots of rubbing compounds and waxes out there. I've tried several (3M, Starbrite, Prism Polish) and haven't noticed much difference in performance. Don't listen to anyone who tells you one or another is the best unless they've done two sections on the same side of the same boat using different products and then compared the results after time. Some are a little easier to use than others. That said, I've gravitated toward using the Maguire's products (Power Cut Compound, Cleaning Wax and Pure Wax).
Clean the stainless steel. I use Brasso. I also clean the brass portholes, but other owners feel that the green "patina" is a form of beauty mark.
Varnish the exterior wood doors. I've used Helmsman Spar Varnish and Pettit Captain's varnish, but am not particularly pleased with either. They both need work annually. There are lots of other choices. I'd like to find something more durable.
Oil the unvarnished interior wood. I use Old English Lemon Oil. (Walmart $3.47)
Launch and have fun! Take satisfaction knowing that your boat will provide reliable service. I've found that my boat has needed fewer repairs as it ages. My last few cruises haven't required any repairs more complicated than tightening a few screws.
Rich