If you haven't already, check out this timeless post for how to get started and what to look for on your initial boat inspection.
Boat Inspection Trip Tips
Definitely, have a digital copy of that posting ready to take with me. Don't fall into the category of individual someone is comfy with using an awl and some of the other more learned skill-sets mentioned, but within my scope i plan on investigating and noting very thoroughly.
Not clear on how the multi works out better for computer etc... they present other challenges - usually homebuilt, often less space, moorage challenges with the extra beam, and so on.
My thoughts on it, while more of a problem for slips, and I imagine tighter quarters mooring definitely present a problem. The added stability, there primary strength from what I have been able to gather, could be an asset when working for hours from an anchor or mooring ball? And when trying to maintain line of sight communications with shore when a bit out from the wifi access points... thoughts not a sale maker/breaker definitely, but something rolling around in my mind due to my carreer choice and primary method of supporting my travels.
Clearly your budget is rather limited since you looking mainly at near 40 year old boats. There's no need to look at something that's been 'rolled and dismasted' at some point - plenty of boats out there - you needn't knowingly inherit those kinds of issues.
My initial budget is rather limited. I do have a pretty solid income, however it seems to go elsewhere before I can put it into anything, my overhead on land has become pretty rediculous. I am minimizing and reevaluating alot of things to fit into the long term plans for my life. I have to live in SF bay at this point for work, and IF I end up getting an apt/house/whatever I see it as beginning the same overpay for a year cycle sucking all the money I could have been using for more important things into supporting a box in a bigger box in a.. well you get the point. So the initial pool is low but there is time and effort. Will avoid the rolled boat though, was thinking so, thanks for the direction on that.
I trust you know of Yachtworld.com, Sailboatlistings.com and other similar sites for searching specific age and price ranges.. they may open up the list above to other opportunities. Similar aged Cals, Rangers, C&Cs, Sabres (and many others) would all fit the bill and give you more different things to look for/like in those size ranges.
I do, and will keep digging till I find the one that fits my needs..
Thanks for all the input.