InfinityMPG

Same here. They can probably pick up on the cues of me cycling there (cycling jersey, tights, sweat, helmet head); but if you ask an employee if it's okay to bring in a bike, then they may be forced to refer to an official policy or seek out a manager, whereas if you're simply responsible and keep your bike from getting the room dirty, there shouldn't be a problem. It's like Leave-No-Trace Camping. Be clean, pick up after yourself, respect the space.

OP's questions have mostly been answered, I'll just add a couple things: a person above said you should book in advance and get agreements in writing. That may apply for Airbnb, but I disagree in the case of hotels and motels. When I hotel tour (places bike-toured: California, Oregon, Washington, Colorado, Georgia, Alabama, Louisiana), I do not book rooms in advance because I do not know exactly how far I'll ride, and it works out. I've run into hotels with no rooms left, but there are always more hotels nearby. I leave a little in my physical "tank" for the hotel search, just in case, and I decide on-the-fly which city or town ahead looks like a good place to stop.

If a hotel ever were to tell me that I cannot bring my bike inside (it has never happened yet), I would just go to another hotel. I do not travel with a lock because it's a waste of weight, but that means that I have to keep my bike in sight, which means in my hotel room.

As for early check-out, it was suggested already, but just pay in advance and tell them your plans. One place in particular put out a light breakfast just for me since I told them I'd be gone before their normal breakfast hours. In my experience, places tend to be nice when they know you're just going to be there to shower, sleep, and head out early. Be nice back, of course