Outlaw, I have to agree with Both KSSS and Swannny...first, you definitely have a nice budget to start with and better than most for sure...KSSS is right though, it will definitely go quick with getting all that stuff. Swannny is correct also with some points...some points or things to think about is, if your going to haul the loader and attachments in dump trailer, what are you going to do when it's just a one day job, let's say and you have the dump trailer loaded..make multiple trips to get the equipment then to I assume.
When it comes to the machines and brands, the advice I got from everyone on here recently when asking about trading my wheeled loader for a newer one came down to a few things..first, what dealers are in your area? Find out who has the best dealer support, etc..it sounds like you already have Bobcat there..what about Case, Cat, etc..dealer support is huge from what guys say and it's true..also, as Swannny said, I would demo all the different brands to see what u like before you go and buy..the last thing u want to do id buy a machine u think u like, then are in it for a while and don't like it. There are guys on here that I'm sure would attest to that happening. KSSS had even mentioned to me when I posed that question before, to actually even try to have all the machines you are looking at on the same job, trying all the same things so you get a good comparison..I would also agree with looking at a low hour machine to buy vs brand new..it's kind of like the whole saying when you buy a new car or truck, the minute you pull it off the lot you lost $$$..you can find a great low hour machine and save a good bit...
If I were you, with your budget, I would price out the cost for the trailer and all the attachments you want, then you can back into what you want to spend on a machine or vice versa. I would also leave yourself some wiggle room as far as money, in case you have those slow times..