i only wish i had some connections to put my 706mkiig on top of one of these towering high rises in downtown denver.
talk about a 1000ft high antenna!!!!
while talking from a 10ft up apartment
Find out who owns or maintains the buildings. They allow commercial ventures and cellular companies to install antennas and equipment all the time for a fee. I had a friend years ago who occasionally was able to bring his CB radio up to the top of a 21 story building and hook it to an 18 foot antenna that he put up there, just because he got friendly with the building's superintendent and threw him a few bucks! Ya never know until ya ask!

Having negotiated some of those siting issues for equipment on the top service floor, elevator house and antennas on rooftops it is a real crap-shoot as to how savvy that piece of real-estate is worth. A few times they just want us to pay an estimated part of the electrical bill for the outlet. Other places have air conditioned suites and go so far as to charge by the square footage, BTU's, wall penetrations and putting antennas on the roof.
Stressing that this is an amateur radio system, operating at no cost (and no profit) will be to your advantage. You want to emphasize that you will have "professional installers" and not do anything to damage the roof. They may ask you to do an intermod study if you are co-locating with public safety or paying commercial customers. Your work up there needs to be "better and more professional looking" than the commercial gear that may already be in place.
The easiest customer I dealt with? The facility managers for a >30 story building in Atlanta with an air conditioned suite with raised flooring (for free as long as I used less than 6U of rack space). The worst? A cellular company that had it in their contract to allow for site co-lo's and access for a municipal customer. (wanna make a bet it got terminally ugly when it came time for contract renewal? The city "suddenly" decided that the public land that was being used to drive across to get to those sell sites was going to be paid for with a hefty rent.).