you are exactly where a lot of sailors are.... and others have been before us. you cant get much more room inside and still be a trailer sailor.... you can absolutely trailer a larger boat, but it becomes way heavier to trailer and the rigging of it is way more complicated and takes longer..... I really liked a catalina 27 I looked at before purchasing my mac 25, but quickly saw it was NOT the boat that was going to be easily and quickly rigged by two people without a mast hoist.....maybe when I get to old to rig and de-rig my 25, I will trade up in size and just keep it moored, but until then I get to trailer it to different bodies of water for long weekend getaways. there is something about exploring new areas that is hard to imagine having to be moored in a marina forever, or at least until we decide to cut the dock line and sail off into the wild blue to parts unknown.I also have a 1984 Mac 25... After 5 years I just have it where I want it. I installed a Furler, put in an A/C unit, got a new outboard, single hand mast raising system, flat screen TV, replaced running rigging, bilge pump, battery charger, recovered the interior cushions, and more.
It has wheel steering, topping lift, shore power, the pop top canvass in great shape and it looks like I am the only one who used it. It looks new and is in great shape too. The problem for me is I now want a bigger boat and it looks like I will have to start over... I just haven't figured out how to make it bigger.
Most of the pricing I see above seems right. I did buy it from Craigs List too. I forgot what I paid but it was probably 3k.
I am also spoiled as I want a water ballasted centerboard or swing keel boat that I can trailer. Or a shoal keel at the very least. There is a lot to said about a 22" draft.
If the Sailboat only had more room...
but I am curious if there is anything much bigger and as simple to rig as a mac 26, for being a trailer sailor....