John--well done.
I would spend many hours on the boat, opening everything, closing everything. Turn everything on and off. Walk the deck in bare feet. Pull and push. Is the boat clean and solid? Stripped screws, scrapes? Doors, drawers aligned? Hardware clean? Cushion snaps all present.? Seals and weather striping pliable?
Sit and observe. Relocate and sit again. Be methodical. This is a complex and sophisticated boat.
A large purchase is worth your time inspecting the boat in detail.
For the engines, get a certified Mercury mechanic, not a yard guy to pull the engine reports. Note: finding a Verado mechanic may be a challenge.
Any engine faults? Hours?
Do a compression test at least.
If you select a surveyor, select one that is very knowledgeable with Boston Whaler's as the construction is
very different that all other brands. Many say they know whalers but don't.
Moisture meters are not a good tool to use due to the fully foamed hull. They will give inaccurate readings.
There are 48 drawings of your 2006 year model 270 Outrage. Note, refer to your boat by its full name. If you call it an Outrage 27 readers will think you have a completely different boat, the Whaler 27.
To get the drawings, enter the year, family (Outrage), model (Outrage 270 and document type (Drawings) [at the link below]. Note they also have the Owner's Manual, too.
Click on the down arrow to download the PDF's. Save to your computer.
https://www.bostonwhaler.com/resources-and-maintenance.htmlThe aluminum tank fit in a finished cavity under floor. They tyically last more than 25 years. As you can see from the drawings, there are two inspection ports on the fuel tank cover. The cover can also be removed, but that is some effort. With the owner's consent you can remove the cover but that is a bit much. If the boat is very clean and the gelcoat is polished, I doubt there is a concern about the tank or hoses. The smell of gas may be a good indicator.
This is the drawing for the fuel tank system.
https://www.bostonwhaler.com/content/dam/boston-whaler/technical/resources/270-Outrage-Fuel-System-Installation-and-Parts-List-2006.pdfThe key areas to inspect are the through hulls. For each, inspect the inside and outside to ensure they are fully sealed and not damaged. Look for weeping, water drip marks.
Given the boat's age, as a precaution, I would replace all the through hull fittings to ensure proper waterproof seal (using a marine sealant, not adhesive) and all the fuel hoses (fill, vent, and supply) with fuel hose that is rated "alcohol resistant" to ensure they can handle ethanol-gasoline blended fuel. All of this work are DIY tasks, with parts available at your local dealer or marine chandlery.
The advice above comes from 20 years of hands-on knowledge of whalers. Currently own my third. I have done a few inspections over the years.
Any more questions?