1. I would just wait until fermentation is done and then add a few days before you rack to secondary. If you need gravity readings to help you judge this, then use gravity readings. I feel like I get a cleaner base beer if I just give it 2 weeks or so.
2. I recommend against just racking directly on the fruit, and I especially recommend against doing it in a better bottle or carboy, especially if you are using a 5 gallon one. When you rack directly onto the strawberries you are going to get a billion little bits of strawberry in your beer that is very difficult to filter out when you want to package it later. You know those little tiny seedlings that are all over the surface of the strawberries? They just float around in your beer and are nearly impossible to get rid of completely, unless you invest in a filtering setup. For my first few batches of this I ended up with bits of strawberry in every bottle that ended up in people's glasses. A 5 gallon paint strainer bag can be bought at your hardware store, Lowe's, or Home Depot for a buck or two and significantly reduces the effort involved with managing the fruit.
Regarding the better bottle, the problem is that a) you won't be able to fit the fruit + beer in there, and b) when you rack the beer onto the fruit it is going to start fermenting again, and it will get EXPLOSIVE if you are using a 5 gallon carboy or better bottle. I am talking about painting strawberry beer on your ceiling, if you're lucky. I am speaking from experience in this matter.
If you use the paint strainer and a 6.5 gallon bucket, this is an extremely painless process from start to finish. If you use no strainer and/or a carboy, it becomes a pain in the butt.