(1) They should be happy for the chance to improve their credit with a utility bill but I know the unknown of utilities are a fear for young renters (our demographic).
(2) Maybe it is looking a little dated. We have had the building for a decade. This unit got a 100% new bathroom at that time. It has had fresh paint about 3 times but it could be due for a little lipstick. Upgraded SS stove a few years ago when the other quit. The white fridge works but doesn't match the stove. Maybe we can find a small SS fridge for $1000 if the new tenants care, but I don't even have SS in my house because I think its irresponsible to get rid of something that works. The entire building has needed some electrical upgrade and a new roof since we owned it. Overall it still makes money, and would with the $100 decrease but, who doesn't want more money?
(3) Any quick tips, other than paint, to make it shine?
(2) Well, that's a problem. By your own description, your building looks rundown, with appliances that don't match, a bad roof, electrical issues, is in need of paint and has who knows what other visible deferred maintenance? Mismatched kitchens and poor maintenance send a powerful message that the landlord doesn't care. That attracts potential renters who also don't care or who know they can't afford anything nicer or worth their effort to maintain. Quality units tend to attract quality tenants. You've dropped the rent in the past and now the market is pressuring you to do it again. As your unit deteriorates, so will your rents and the quality of the tenant pool. (Your appliance argument is weak: sell the white one and buy a used SS or vice versa so they all match. Someone will be using them, so they won't be wasted.)
(1) This sounds rather condescending.* Could you frame it more positively? Something like "I encourage conservation by having tenants manage their own utilities." Also, older appliances tend to be less energy efficient. As a tenant who knows utilities are not included, I'd consider that a strike against renting your unit.
*So does calling a potential tenant a "looker". Like it or not, a tenant is kind of a partner in your business. Treating them respectfully is key to obtaining and retaining excellent tenants, IMO.
3) You've deferred maintenance for ten years and now you seek a quick fix? Are you sure you are being a good steward of your investment?
To answer your specific question, I have lowered rents directly and indirectly. In a bad economy, I once reduced the rent slightly before seeking a new tenant, because all rents were down, not because my unit was worse than the competition. I have also skipped annual rent increases on occasion to reward an excellent tenant. I have been repaid in longevity, which is worth a lot. Better to retain a good tenant than to miss even a single month of rent.
I have never lowered the rent on a vacant unit because someone asked me to. If they can't afford it prior to move-in, they can't afford it, period. If someone wants my unit, but they can't afford it, I politely decline and seek a better-qualified tenant. Since all my rentals are attractive and well-maintained, I have plenty of applicants.