Really I don't even know how to say this, but I have to say it because I need your help: I have a crush on my tenant. This guy is great, he's everything I wish to have in a partner. Help!
Hooooooooo boy. While I am generally pro - going for it in matters of the heart, this is a different case because there is a pretty serious power imbalance at play here. When a relationship is based in business and money is exchanging hands, the opportunity for misinterpretation is high. Now I'm sure you are a lovely and respectful person but I can not emphasize enough how you must proceed carefully (should you chose to proceed at all). Because while it is possible for love to bloom between a landlord and tenant, it is also possible for it to be interpreted as sexual harassment.
A few questions to consider: How well do you really know him? Perhaps he is just presenting the best version of himself to you because he wants a smooth and harmonious living situation. And hey, what's more appealing than someone showing up to do exactly what they're supposed to, like clockwork, every month? We all want someone dependable! But if dating through my 20s has taught me anything, making rent is not a direct correlation of dependability in other areas of life.
Also, has this man indicated that he returns your affections in any way? Beyond simple flirting has he tried to cultivate a relationship that involves spending time outside of your building? If he does return your affections it is important to let him take the lead and as soon as you possibly (and legally) can, remove the landlord/tenant aspect of your relationship.
Whatever you decide to do, be smart, be respectful, be kind.