I'd go with the Asp. Every time you jump, you have to turn to the next system. I can imagine that becoming very tedious with an Anaconda because of its slow turning speed. plus, that will increase the risk of the Anaconda getting sucked into stars. I just got back from a 34KLY (about 2500 jumps) trip in an Asp. Even with that, it's easy to lose concentration and leave the throttle on when you drop to the new system, which puts you in the star in about half a second. Many times, I woke up and was able to steer just in time. You won't have enough time to steer in an Anaconda. Each time you do it, you lose another 1% to 2% hull and power-plant - worse if you don't have heat-sinks for when you heat up escaping from the star -, neither of which can be repaired until you get home. I think an Anaconda would be OK if you have a slow methodical mind or a high level of concentration, but if you're more inspirational or get bored easily, the Asp would be better.
I learn't a lot on my trip. Firstly, you don't need shields. secondly, you want the fastest fuel scoop you can get. Thirdly, a bit of extra fuel tank helps. After that, make your ship as light as possible by using the minimum power-plant, thrusters and power distributer that you can get away with. I'm going back again later this week. This is what I'll be using. Last time, I just about exhausted the ammo in a A4 AFU, and used 14 of the 16 heat-sinks to escape from stars without damage::
http://coriolis.io/outfit/asp/02A4D...f2i.AwRj4jmyyA==.AwhMI5XTYo==?bn=asp explorer