Will blown in insulation help in this situation

The simple answer is "yes". Every piece of insulation you put in is a bit of heat that's not lost to the outside world. This is better for you as your house is warmer and your fuel bills are lower, it's also better for the environment as you're not using as much energy.

The more complex answer is "it depends". Buying and installing the insulation costs money (you don't say!) so the immediate equation becomes "is this cost less than the money I'll save over X years?". It's the answer to this that will, largely, affect your decision on whether to insulate or not.

The company who wouldn't estimate may be right (for their system) in that it would cost $2,000 (say) to do the work, but you'd only be saving $20 a year on your heating. This would mean it would take 100 years to pay back the cost. Now, if you can find a system that costs less then the proposition becomes more economical. Insulating the ceiling/roof space is a good thing to do anyway.

However, if your primary concern isn't the savings then you might decide to go ahead regardless.

It depends on where you live and how you plan on attaching everything. For interior insulation you want the vapor barrier on the warm side so the colder regions would always do the interior facing and some warmer climates would do the exterior side of the insulation. The underlying rule of where would the moisture most likely be trapped still applies but it typically biased because of installation, how you plan on attaching everything. For interior walls, no vapor barrier is recommended if you use a full fill spray foam because it is a close cell foam (over 2lb density like most spray foam) and is meant to be a tight squeeze unlike most insulation and stops airflow instead of slowing it down. The same can be true for rigid foam especially for outside insulation. If you plan to use contact adhesive, liquid nails, etc glue to hold the rigid board to the house then you'll be essentially stopping all the air flow and that side would not be a candidate for a vapor barrier, additionally if you are gluing the siding on, the same rule would apply.

To sum up: If you are in a cold climate, even seasonally, it is a good idea to put a vapor barrier on the outside of the outdoor insulation as long as you are not gluing the next layer onto the insulation. This will help the trapped moisture wick out better.