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1. There are a few VFR-only airports that do have weather reporting. Henderson, NV comes to mind as it a control tower, but no approaches. (I think this is what screwed the check airman up, since he was thinking that there can't be weather reporting at a VFR airport, but he was in too deep to admit he was wrong.)
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This is correct. As long as it has wx reporting you can conduct IFR operations. If it doesn't have a published IAP of course you can't do a instrument approach (unless you design one yourself and get it approved for your company to use - I've been told this can be done, although I wouldn't know where to start). Remember a visual approach under IFR is still an IFR operation/clearance. Making a "visual" approach under VFR is really a misnomer even though you hear people refer to that all the time. It is simply a VFR approach or an approach under VFR. I believe 135 is supposed to get some admendments in this area when 91 K gets finalized to even the playing field.
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2. Depending on your OPSPECs you can file a company flight plan (i.e. call the boss when you land). Negating the need to open a FAA VFR flightplan after you cancelled your IFR.
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This is true. Most Opspecs allow for company flight plans.
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3. "So technically even taking off, you should not get an IFR clearance until you are airborne." It's been a long time since I've been a 135 flyer, but can't you take the ground visibility and if it’s above takeoff mins use your own observations?
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You are taking - off in VFR conditions under VFR rules. Visibility should be adequate enough so takeoff minimums should not apply. At an airport without weather reporting you can't conduct IFR operations - this means a visual approach or a departure with an IFR clearance. Of course under VFR you are making your own observations and under IFR the pilot can determine whether he has adequate visibility for landing (wx report was above minimums prior to FAF). Using your own observations is a little more tricky for takeoff. You are supposed to obtain and use the wx report you recieve and if it is an automated report, certain parameters have to be there in order to use it. People make their own observations all the time but if it came down to a legal action it may be hard to argue against the repoting facility, especially if RVR is involved. Of course you can get approval to have an official company wx observer at an airport that normally doesn't have wx reporting. The airlines do this (KHXD for instance), but they can't share that observation with other operators due to the liability issue.
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4. Can you file to an intersection under 135? There's no weather reporting!
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Sure you can. You are not making an instrument approach to an intersection. This is how composite flight plans are done. They aren't done often so you may get a controller who questions what you are trying to do. Going to that "VFR" airport after the intersection you use an area forecast. Not the greatest, but meets the legal requirements for what you are doing. You should consider the ramifications for lost comm - you better be sure you can get to VFR conditions at or before your clearance limit. One way some operators do it is that they file IFR to a nearby "IFR" airport, get into VFR conditions, then cancel and procede VFR to their intended airport (best to use a company flight plan). This solves all the scenarios for having weather reporting and a good plan in the event of lost comm. while still IMC.
