didnt i refer you to foxwillow in another post??? .. if so.. get there first.. and budget a couple conifers to star in your future scape ... they will be expensive.. but they will make an immediate impact ... and dont forget.. you can look at conifers in winter .... so there is no reason to wait until summer to go to this nursery ... as for trees ... i find that 2 to 5 footers ... max.. transport easier [presuming you are a one man work force] ... plant easier .. recover faster.. get established faster.. and will outgrow something twice as big [and 4 times as expensive] within 5 years .. IMHO ... planting in your z5 chicago .. should be around 4/1 ... giving your trees 6 to 8 weeks before the real heat of summer hits ... your trees should be fully dormant .. and no matter which type you get.. i would bare root them at the size i suggest.. and plant them in native soil ... [with special rules for bad clay] ... i am not in your BANG FOR THE BUCK club ... i want a tree that is easy to deal with and easy to grow.. all factors become increasingly complicated.. the bigger your bang is ... and.. as to your dream for that upnorth feel .. that cracks me up ... but you better have a ten year plan for that look.. or a multimillion dollar budget ... below are some pics of what took 10 years in my former horse pasture[not counting the giant trees] ... and all but one of the conifers were under 2 foot when planted ... and the trees 4 to 6 foot bare root ... its great that you have a long term goal of that upnorth feel ... but please put it in the proper decade long perspective ... good luck ken that redbud was 4 feet tall 10 years ago

@hosenemesis - Thanks for the great ideas. BTW the one landscaper told he meant "Podocarpus" as he said Privet Wax Leaf and Ligustrum is the same (?). The reason, however, that he is pushing the Texas Privet is that he said it's the hardiest of the 3. I didn't think of the fact that the ivy would grow into the shrubs and yes, it would make a mess. The barrier makes perfect sense but I imagine it won't be cheap to dig up that ivy, cut it back, and then make sure the roots are really gone otherwise if it starts coming back once the hedges are planted, ugh. I'd get rid of the ivy but I think we have it and neighbors too as it helps with the erosion of the sloped portion of the backyard edge. @yukkuri - My wife would love citrus and avacado trees but do they really grow together enough to provide privacy? And won't they get wide enough to take up a ton of room along that wall (the wall is probably about 100 feet or more)? I suppose those types of trees would at least live better with the ivy. @desertdance - Thanks for the Sour Orange suggestion. I'll take a look at it and ask someone at a local nursery. And I thought this part of home ownership would be the stress-free part. Now I'm almost frozen trying to figure out what to do as it seems there is strong potential for regret or a do-over due to so much I simply don't know...and you hope the landscaper suggest what is sustainable and not just to make $$$. Especially the fact that neither of the two quotes said anything of keeping the ivy away from mingling with the shrubs which makes sense that it would happen...and be a headache.

Be aware that conifers do not stop growing. For example, 'Smaragd' will get to 15 feet in roughly 15 years (give or take) from a small plant. In year 16 it wiil be 16 feet, year 17 it will be 17 feet, etc. When conifer sizes are given it is usually for 10 or so years as the ultimate size is determined by gravity and how long it lives ;-) Having said that, arbs are a nice choice but I would mix other conifers in as well such as Picea omorika 'Pendula Bruns', Picea pungens 'The Blues' and Picea glauca 'Pendula'. These were all available at Stein's last year and have about the same growth rate as 'Smaragd'-kinda. Are power line limiting the height? tj

Yes, oriental bittersweet, a vine that will spread invasively via the birds eating the berries and will damage trees with their twining and weight. To tell the difference between American bittersweet (non-invasive Celastrus scandens) and oriental bittersweet (C. orbiculatus) look at where the berries are. In the native version, it's only at the branch ends while on the invasive type they are in the axils up and down the vine. I'd advise cutting it at the base, painting brush killer on the cut surface of the stump, and pulling the vine down to remove and dispose of as many berries as possible.