Re: what whaler for me?
Ahoy, Jim.
Welcome to iboats.
I have owned both a Montauk (1981) and Outrage 18 (1983). I loved them both.
Frankly, I think the Montauk is more versatile. The one "foot" difference is a huge foot.
The OR 18 is a LOT more boat. It is faster, more comfortable in rough water, roomier, thirstier, harder to launch and retrieve, more weight to tow, less maneuverable and more expensive to own and maintain. For the bay and the Potomac it would probably be my choice. I would power it with a 150 4 stroke or ETEC.
The Montauk is a boat for anywhere. A lot less cost, fuel, work. More maneuverable and easier for a solo mariner to handle, launch, retrieve and tow. Not comfy in a chop. I powered mine with a Suzuki DF70 EFI 4 stroke. Other good matches are the ETEC 90 and several 4 stroke 90s. I would go with the Suzi again without a moment of thought.
Your budget limits you some. It probably wouldn't cover a good OR 18 with 4 stroke power unless you find one already powered that way. Twelve Kbux should get you into a pristine, turn key '80s Montauk with 4 stroke power with change for extra goodies.
Continuouswave.com has a Boston Whaler Marketplace, and there are always plenty of Boston Whalers in iboats Classifieds.
Good luck. I think you have picked the right time of year to shop.