I feel that I am at a crossroad with my 1990 Hunter 30. I've only owned this boat for 2-1/2 years now (moved up from a Catalina 22) and have pros and cons about moving up to something a bit bigger (ie; 37-42'). It is just my wife and I plus my 14 year old son that weekend coastal cruises and does an occasional 1-2 week cruise to multiple destinations in New England. When I go with friends, I lack the space for 3 adult berths, unless I use the saloon area and lower the dinette table (still a bit short for most adults and a pain). Here are my pros and cons of going bigger. Any input is greatly appreciated, especially for those that are familiar with the 1988-94 Hunter 30s. Pros: - Aft queen berth is great in a 30-foot boat, not having to rely on the vBerth for couples - Walk-through transom to the swim deck is great when the water is swimmable - Open rear deck is nice to board from the slip when you are backed into the dock - Sips diesel with its 16HP Yanmar 2GM20F (spec shows 18HP but eng plate states 16) - Bought with a 36" helm wheel for nice helm handling when on a heel - Nice balance of finished fiberglass to teak in the cabin and on deck (not too much teak, but a nice amount to provide the somewhat classic look newer production boats are missing). - Seasonal slip and over-wintering prices are decent and not too crazy as going bigger - Only one head to maintain, fairly simple plumbing & electrical Cons: - Cockpit is really only good for 3 people, 4 is a squeeze - Getting around the helm wheel is a pain since it is oversized - Too small to effectively mount dinghy davits on the stern ... would close off the aft view if tilted up, and eliminate the rear boarding feature - In-counter ice box is deep, but no refrigeration and freezer ... having to restock ice, drainage to the bilge is just a dumb design idea! - Limited storage for longer trips (provisions and supplies) - No aft cabin closed doors and no shelving or cabinets for clothing and gear - 2-burner gimbaled alcohol stove/oven as opposed to propane or CNG - Tight around the dinette table - No windlass, costly and not ideal to add one on this boat - foredeck barely fits the inflated 9' dinghy and is in the way when anchoring - Only room for 2 batteries (squeezed in 2 group-31s, barely) under aft berth for 210AH total Part of me says to stay with it since I have probably $20K in additions over the purchase price (bimini, dodger, batteries, B&G Triton T41s, Vulcan7 MFD, B&G controlled Auto-Pilot, new Blue Sea 40A charger, with new wiring & circuit protection, Ronca 35LB anchor on Mantus Bow Roller). This boat also has the rear stern pushpit seats that you usually only find on a H30 from 91-94, and a second cabin top winch for use with my Asymmetrical Gennaker. My guess is that a late 90's to early 2Ks Hunter for maybe a 37.6, 376, 38, 42 Legend series or other would be in the $50K range, with the 42s in the $80-120K range. With that also comes additional marina fees, higher maintenance costs, etc. It would give me more room, a more spacious aft berth with storage, but not so much more on the area of a roomier cockpit or ability to sleep more than 2-couples (bow and stern). I'm 50 now and would love to be on the boat more and more, but not too likely until I am closer to 60 and retirement (unfortunately). So, I am leaning on saving the money and just sailing the crap out of this boat as much as I can. But, it is the simple things that just keep bugging me .... lack of windlass, lack of storage, lack of cockpit space. I feel like I am always moving stuff around when I head out for a while since there is no dedicate space to store everything (tools, spare parts, extra rigging, even fenders, etc). Rear swim lockers and under rear cockpit seat areas are all the storage I have outside of the cabin. In the cabin, I only have the vBerth lockers for clothes and PFDs and under the dinette seating and settee for food and drinks and other supplies and tools. Thanks for any insight into this and for lending your ear to my rant!