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If you really want to date your landlord badly and minimize conflict, move out after your lease is over with or pay a penalty fee and find another place. If that's too much for you, as it would be for most people including myself, don't try to get romantic with her. At least not until after you have to move out for whatever reason- most ideal reason- you're buying a house!
I just keep thinking your early to mid thirties is just one of the better stations in life for men to date.
In your early twenties after you leave college, dating can be a struggle for guys women your age often prefer older guys who are more financially established. Dating gets better for guys after 25 and between 27 and 30 dating is probably equivalently easy for both men and women. But this is also the time when lots of people are exiting the dating pool to get married and start a family.
For women after thirty, the quality of their dating pool is starting to drop off as more of their dating pool consists of guys with kids from past relationships. So a single 34 year old guy who never had any kids is a pretty desirable thing to find for these women.
I get that the OP is an introvert, but instead of trying to date the woman that is most convenient (your landlord). Why not try to date the type of woman you are most interested in?
A single 34 year old guy with no kids is a valuable thing to find for women in in their late twenties to women in their mid thirties. Is a woman ten years older than you really what you want right now?
If you ever want to get married and have kid, this is a great time in your life to find a woman willing to do that. The women in their early thirties late twenties have lots of friends getting married and starting families and a lot of women this age would be willing to do that with you.
And you are thinking about going after your landlord who seems to have another rooster hanging around the hen house? Why bother with that? You have a nice living situation. Your landlord wants to befriend you. Why not do that instead?
If you try to hard sell yourself to women you are trying to date, you come across as an insecure braggart. Women will dismiss your statements as stuff you tell all women because you are trying to get laid.
But your female friends can and will talk you up to other women and women will believe and trust your female friends because your female friends aren't trying to sleep with them. I personally have benefited from potential girlfriends taking with my female friends and my female friends singing my praises in ways I never could, but you need to have female friends first to benefit from that.
There are huge advantages to having lots of female friends. Women read other womens intentions and actions much better than guys do. So it's really useful to have some actual female friends you can turn to while being a single guy.
Your landlord seems willing to assume this role in your life. She really seems genuinely interested in treating you like a friend. You are somewhat new to the area, so you probably don't have many female friends. Here is an opportunity to pick one up.
I dont know why so many people are saying you need to leave. If things ever go south, you can always move then.
As for the short term, I would let things flow naturally. If you find a time to hit on her, do it if you feel like it. The only thing I suggest, is DO NOT go in without clear signs. Do not try to randomly kiss her or something like that, it could make things VERY awkward. Let her lead you a bit and make sure you have multiple flirts back and forth before you bring up anything between you two.
On another note, do you really want to be with this woman? She is a little old for kids, so not sure if that's in the cards if you two date or not. Make sure you're honest with yourself about what you want, and clarify what SHE wants before you continue a relationship.
A few months ago I (M34) moved to a new city and via an online rental ad site came into contact with a woman (F44) who had her own apartment with a room to rent, and after a video meeting she offered me to rent it. It felt a bit weird as a straight man to move in to live with no one else than a (straight and single) woman, perhaps especially the fact that she accepted me to be her housemate, but I accepted the offer either way, especially since my room has its own bathroom which is a big advantage obviously.
In the beginning of us sharing apartment I still had a girlfriend, and therefore kind of forced myself to not think about my new housemate as anything else than a housemate/platonic friend. But I definitely noticed she was very good looking, as well as charming and fun to be around. During this time she also made great efforts to ask me if I wanted to join her for different social events, both with her friends and with her family, so I have also come to get to know her family and some of her friends a bit.
During this time there was never any flirting between us or anything like that, although she did ask me a couple of times if I wanted to watch a movie with her, something I declined to however, mostly due to my girlfriend. We also talked a bit about relationships, and she told me that her previous boyfriends had been younger than her, like around my age.
As I said before during this time I forced myself to not try to look at my housemate in a sexual way due to my girlfriend, but after a while me and my girlfriend broke up (something that didn't have anything to do with my new housing situation/housemate, I might add), and this is the point where I could "allow" myself to start looking at my housemate in a bit different light. And also I must admit that the whole situation with us living together but not being in a romantic relationship has continously made it more and more exciting for me. She works out a lot so she has a very nice body, and she often wears quite revealing clothes in the apartment (although perhaps not anything overtly sensual, nor in only her underwear or anything like that), so whenever we stand talking I must really force myself not to simply stare at her body.
I am unfortuntaly very shy when it comes to girls and flirting and all that, so I haven't really made any move on her or tried flirting with her at all (also due to the fact she's not only my housemate but also my landlord, so I wouldn't want to make a fool out of myself and risk being kicked out of the apartment). For her part, apart from what I said above, she did at one point tell me that I have a fit and muscular body (as I work out quite a lot), and at another point when we were talking a bit about relationships in general she told my that she thinks I am very good looking and could easily get a girl in the city lol. Often when we are both in the kitchen (it happens quite a lot that we prepare food and cook at the same time) whenever she needs to get passed me to fetch something in the cupboards she puts her hand on my shoulder or something like that, very gentle and innocent but still a very good feeling.
I would really like to have a more physical relationship with this woman. However, during this last time she has started dating another guy, although she's never told me explicitly that they are dating or in a romantic relationship but instead that they are just "friends" (not that it is my business in the least, but she still has pointed this out to me). I would lie if I said this hasn't made me jealous, although she is obviously free to do whatever she wants.
With this being said, is there anyone here who could perhaps give me some advice on how to proceed - or not to proceed - with this situation?
You're stuck in the friend zone of your housemate. It's a classic case. You've positioned yourself as the nice guy and she's comfortable with that. You've got to change that.
You're putting her on a pedestal because she's good-looking and you've never had a shot. It's the same thing that happens to guys who've never had a girl interested in them. You need to get out of that mentality.
She apparently thinks you're good-looking. Great. So that's your cue: you need to start flirting with her. If she rejects you, then you know. But if you never try, you'll never know. And watching her date another guy will only make you more bitter.
Start by increasing your physical presence. When appropriate, touch her arm or back when you talk to her. Hold eye contact a bit longer than normal.
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