It may not be that bad... I rent to a lot of people visiting from other countries who seem to ask more questions like these but those tenants are often my better ones. Some folks are just more worried about contracts in general or consider it more of a negotiation. I don't think I would pass someone over who wanted to clarify... maybe just check their references really well. A fastidious renter is way better than the alternatives.
Renting and moving are stressful, and there is a certain amount of faith involved. This person doesn't know you are an honest, upstanding person. This is a great opportunity to set expectations and let them know it is a business for you (I have failed at this in the past and been taken advantage of). If you have a waiting list of 10 people, tell them. You set the rent based on the current condition... improving the condition may increase the rent. People just don't see it this way until they have to choose between better condition or lower rent.
For the cleanliness issue... some folks just have different standards which you can probably never live up to (like my mother dusting my ceiling fans every visit). My new procedure is to tell them I have $150 budgeted for cleaning and they can either (a) accept the cleaning crew I normally use (b) keep the money or (c) hire their own. They are then in control of the scope of the cleaning and if my cleaner isn't good enough then it was their choice. On move out I also give tenants the option of paying for the same service so they don't have to clean. They often take this offer. This saves money because the tenants never do a good enough job and I have to hire someone anyway.
I do something similar for carpet cleaning... some folks want them cleaned and some folks don't even notice. They are white carpets and always look a darker in traffic areas like the stairs. If I pay for it I ask them to pay for the same service when they move out. People seem to think this is ok.
For painting, if it is a 5+ year old paint job or has rooms with weird colors I tell them that I will paint 1 room of their choice in my choice of matching neutral color. I have a guy that will paint any room for $100... Usually this makes them happy and allows them to ignore all the other banged up walls, helps keep my house nice, and is way cheaper than painting the whole thing.