Do yourself a big favor, one that is guaranteed to save you a lot of money down the road. Whatever method you use to mount the gutters, install a metal drip edge first. I just finished replacing the first two feet of roof all around a house that did not have them. The only way to fix it was to remove shingles and rotted decking and replace, not cheap. Drip edge is about $1.00 per foot, what I had to do was considerably more.

Update: the roofer came back and checked all of the gutters and confirmed that there is no drain pipe outlet into the gutters, but we couldn't figure out where the drain pipe ended up. However, he did find an old downspout tucked away in a weird spot in the soffit, and removed a large clog from that, so I started the AC again just to see if the water would start draining there. It did not, but water did start dripping from another area of the soffit (halfway around the house from the unit!). Anyway, it was obvious that we weren't going to get any answers without an expert. So I called in an AC guy, who quickly figured out that the drain pipe runs down into the basement (why go all the way from the attic to the basement instead of out into the gutter?), and that it was badly clogged. He blasted out the clog and added a union so we can easily shop vac it ourselves now and again, and all was well. He also installed the overflow emergency switch that the previous owners left sitting (unconnected) in the drip pan. Grrr... The relationship between the soffit/gutter work and the leak is still a mystery. It could be coincidental, but my guess is that the drainage pipe has been clogged for quite some time, and the only reason we didn't have a major indoor leak before now is because the water was seeping into the soffit and slowly draining through all of the holes that the roofer patched (in addition to some large holes in corners/dormers, he also patched about a million small carpenter bee holes). Regardless, all the water is now going where it belongs, thank goodness! I've got a dehumidifier running in the rooms that got wet, and I'm hoping we can get away with just repainting the ceiling rather than replacing all of the drywall. I do worry about what might be growing inside those soffits, though - the gutter guy said a ton of water and debris came out of the old downspout, so I can only imagine there's more where that came from. Thanks for your guidance as always!

Hidden downspouts are an accident waiting to happen...maybe not immediately, but some time in the future. I once had a set of gutters and downspouts with the end of one gutter buried in the siding. That end of the gutter inevitably leaked, but the siding didn't show anything until I noticed a slightly odd looking spot on the wall it was butted into. I pulled the siding and found the 2X6's that supported the wall had turned to mush and a moisture ant colony had set up home inside. I had to completely rebuild the wall. If you have downspouts with their many connections hidden from view, you will have a problem. I've owned homes for 4 decades and have never had a gutter and downspout system that didn't periodically leak. As for your plan to have an unorthodox connection to the drainpipe, I suspect that that is just going to increase how soon you have a problem. I know this is not the answer you wanted, but I urge you to reconsider how you are approaching your rain handling system.

Yes the pillars are structural I am not sure if they are all needed but that will be determined by a pro. As for colors A nice shade of gray/ green with that roof and brick will be nice I would remove the shutters since most of them are too small anyway.Your gutters need to be the same color as the roof they are not a design element.Maybe just wood cladding for the pillars painted the same as the trim in the green some nice big planters by the door with seasonal plantings and then decide on a door color