Adding Insulation to Exterior Walls

DIY vs professional probably has more to do about your skill level. If drywall, you could take out the bottom 2' and run insulation up the walls. Can be a bit of a pain in the arse in sections with switch boxes, but have done this to a small utility room

I have never worked with blown in insulation, but I think they run that from the top of the walls (not sure how much they cut out). If you don't want to run the fiberglass insulation, I would look for quotes for this from a few companies.

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If you don't want to start ripping out sheetrock then consider this option (or something similar):

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Something like that is the only thing that I can think of. It is not ideal, but it would be a lot better than nothing.

What is the benefit of drilling in from the exterior wall instead of going in through sheetrock?

My guess is since it’s all vinyl siding they can take a piece off, drill the hole, and replace and don’t have to go room to room. However with it being a 2 story lifted house it might be easier to do it from the inside

I did blown in insulation in one of my rental units. Drilled holes at the top of wall between each stud and ceiling (wanted to blow insulation into area above ceiling to see if it would dampen noise from upstairs, it didn't). After I blew in insulation, I installed crown molding to cover holes. If I were doing this at a camp house, I would do a much simpler molding. Did it help? Maybe a bit but not enough to justify the amount of work. But this place has a brick facde, then a 2" void, shiplap sheathing, studs, then plaster, its an old place.

Also have to take into consideration that there may be/should be fire blocks.