Question about shopping districts in Portland

[DizzyEdge]

Hey there, I visited your fine city last week, and loved it. One thing Portland has that Calgary is behind on is block after block after block of small scale mostly independent retail, creating interesting streets. Examples are Alberta Street, NW 23 Ave, etc.

Question I have, if a larger retailer (think say.. Walgreens), wished to purchase up a block side on any of those streets listed above, demolish the existing multiple stores, and put in a new building (perhaps with some condo apts above) with just Walgreens as the sole ground floor tenant, creating a wall of windows (some of which may not really show the interior of the store) but one set of doors, would that get approved? If not, what specifically would be the deal breaker as far as regulations? It's a problem we're having here, either 4-6 small stores get torn down and one single retailer like a drugstore or bank goes in, or these types of retailers fill existing gaps in streetscapes, curious if there are regulations in Portland which would prevent this.

Thanks!