Andy, There are other programs than iPhoto (i assume that is the one you are talking about for managing your photos.) A rule of thumb that i think i would give for macs, after my 10 or so years using them. Macs and their accompanying software will address 80+% of people and what they want to do, imo. Once you get beyond that, and have expectations beyond that, you might have to look to the mac community for software. It is well known that iPhoto has a hard time handling a large number of photos. (I admit "large" is a variable term.) But i have a friend who is in your boat, and there are several other applications that are designed to handle that amount of photos. iPhoto is an app that is supplied, and for most people, about 80+%, imo, it will do the trick, BUT it will not work for ALL people and ALL situations. No software will, imo. There are a LOT of people the Xywrite doesn't work for. I gave up trying to convert them because, that's the way it is. What i WILL say about the mac, with you having thousands of photos on your mac, i would say that moving those photos to another app and dealing with them, i think will be an easy process. BUT by all means, if a mac doesn't work for you, find something that does! Some people like macs (there are a lot of writers AND btw, a lot of different word processors geared toward writing on the mac.) IMO, for the artist, they need to find their tools. For some, they like the mac. For some they don't. Simple as that. If i can help in any way, please feel free to contact me offline! Russ