A 5yr. plan to a cruising retirement
The Out Island series offers a lot of liveaboard space for the dollar. They were quite roomy for their day and had a simple but very workable interior layout.
As sailboats they are very mediocre sailors especially when it came to beating to windward. Some of this reflects my own prejudices toward faster and easier to handle boats. I really do not enjoy sailing slower boats but more than that, I really hate to run the motor and so prefer boats that sail well because it means that there is substantially more sailing to motoring time. All boats are a compromise and trade offs are made to accomplish specific goals. In the OI series, the goal was clearly maximizing accommodations which took precident over good having more sterling sailing abilities. If you are trying to develop sailing skills these are probably the wrong boats as they are comparatively numb to sail.
The quality of the constuction on these boats apparently varied pretty widely over the course of their very long constuction period. I have been involved with OI''s that were very poorly constucted (with hull deck joint problems, poor hardware and hardware attachment, junky electrical installations etc) but have also seen postings from OI owners that descibe their boats as being constucted to a higher standard.
One gripe that I had with these boats, and my experience was actually with the smaller OI36, was that they did not have very good ventilation.
Most of these boats are getting a little long in the tooth and are bound to have some of the older boat blues. There is a Morgan OI series website but I apparently have misplaced its bookmark in my computer.
While I personnally have never liked these boats, they do have a cult following who seem to love them and defend them voraciously. So, if your concern is finding an inexpensive liveaboard that you can motor up and down the ICW and occasionally sail, then the OI41 offers a lot of boat. Some other boats that you might look for with similar virtues and perhaps better construction and sailing abilities are the Morgan 43, or the CSY 44 (or the earlier and rarer 41)