It all depends how SP friendly the place is...
Back in the EE heyday, I was visiting one of the smaller motel/hotel in the NW end of the city almost weekly (ahh, memories). The guy running the place became quite friendly, and would often give me preferential treatment or the better of the rooms that were available. Some SP's working smaller hotels I have spoken to are considered preferential clients by the hotel due to the steady business they provide to the place and are apparently treated very well by the staff. One even told me that hotel staff would send her a complimentary fruit basket or room service.
Other hotels, particularly the larger ones, seem to discourage the hobby, and are quite hostile about it. As I recall there was a lot of hassles being discussed about the Chelsea (I think?) a while back where guys were denied entry unless the lady came down to meet him. No way to possibly be discreet in that situation.
Regarding condos, what I don't understand is why some of the popular agencies that happen to be advertisers on this board (hello: Toronto's Finest) would choose a building that requires "guests" to sign in and out at the security desk and give a vehicle licence plate number. I was at one such place recently, and the clip board list had a full page of guests with short visit times to a few select suites. Would not be too hard for the security guard to figure out what was going on there.
What was worse, one time when I was leaving their place, there was a LE officer standing at the desk, chatting with the security guy! No fucking way was I going up to the desk to sign-out after an hour visit that time, and fortunately the desk guy did not notice me. Given the history of the municipal region this location was in, I was especially concerned.
I also wonder if condo security has the right to ask for ID like they do when you book yourself into a hotel or motel? I was asked once to show ID by condo security, and I had to flash my driver's licence, but nothing was recorded, sort of like when getting into a bar. I figured I had no choice since it could be considered suspicious if I did not comply, or suddenly decided to leave, so I played it cool and did as asked. Never went back there again.
If I can, i always park off-site at a condo so they have no reason to ask for my plate number, and if they ask me to sign in, I rarely will ever go back to that location. Oh, and to the OP: do everything you can to avoid calling or hanging around the lobby of any type of place...call from a remote location and walk straight in with the access info as if you own the place.