u/Born-Good-4830

I'm looking for advice from landlords or property managers who have dealt with high-maintenance tenants.

I own an older rental in a very tenant-friendly jurisdiction. I'm proactive about maintenance and fix issues properly, but as expected with an older property, things come up from time to time. I've been self-managing this tenant for a few years, but I'm ready to hand off the maintenance and day-to-day management because I really don’t have the time and energy for property management anymore.

The tenant previously escalated a significant maintenance issue to the local housing authority. It was ultimately resolved well, and our relationship has improved since then, but they still seem demanding and may escalate concerns if they're unsatisfied. On the other hand, they always pay rent on time, follow the rules, report maintenance issues promptly, and are otherwise reasonable.

I'm deciding between two property management companies:

Company A

• Pros: Boutique firm recommended by my attorney. Experienced with difficult tenants, lease enforcement, and has capable in-house maintenance.
• Cons: Higher fees, mixed/polarized online reviews, and I worry they may come across as too confrontational and increase tension.

Company B

• Pros: Larger, more established firm with excellent online reviews. They seem to have streamlined maintenance processes, are well regarded by tenants, and tend to manage properties that are already well maintained (which mine is).
• Cons: I'm unsure how experienced they are with tenants who push boundaries or threaten complaints, as they seem more process-driven and less personal in day-to-day interactions. Their in-house maintenance is also limited, so they'd rely on outside vendors for more complex work, which may not save me much compared to using my own contractors.

Given this situation, would you choose the firm that's stronger at conflict management or the one that's known for building positive tenant relationships with streamlined maintenance process? For those who've hired PMs for challenging tenants, what qualities ended up mattering most?

My husband and I are deeply incompatible personality-wise, and over the years I've increasingly felt like he's dragging me down.

I'm creative, intellectually curious, outgoing, and have a strong social circle. My husband is the opposite—very reserved, with almost no close friends, little curiosity, and not much initiative. We both went to good universities and have good jobs, but I honestly feel we've always operated on different levels intellectually. Appearance-wise we're in the same league, but personality-wise the gap feels huge. We are still physically attracted to each other. 

People often ask why we got together. We met right before the pandemic and moved in together quickly because of lockdowns. Looking back, I don't think we'd be together if we'd met under normal circumstances. Early on, he seemed charming, romantic, confident, and socially engaged. Only later did I realize he lacked a strong sense of direction and self.

The bigger issue isn't our personalities—it's that I've lost confidence in his judgment. Throughout our marriage we've made several major financial and investment decisions. I do extensive research before making decisions, while he often avoids thinking things through but still influences the outcome. Looking back, many of the decisions he pushed for turned out badly. Whenever I'd ask why he made a particular decision, his answer was usually, "I don't know," or "I didn't really think about it." Over time, I've felt like I've had to carry the mental load while being held back by his indecisiveness and poor judgement.

To be fair, he's a genuinely kind person. He loves me deeply, treats me well, and I don't question his intentions. But I've realized kindness isn't enough for me. I need a partner whose judgment I trust, who can think independently, and who can help protect and support us through life's difficult decisions.

After years of encouraging him, he's finally started individual therapy. One of the biggest things he's realizing is that he has very little self-awareness about what he actually wants or why he makes certain decisions. His therapist has encouraged him to practice reflecting, becoming more introspective, and developing his own preferences instead of drifting through life. It seems to be helping, but after seven years of feeling like I couldn't rely on him, I'm no longer sure it's enough. I've lost so much respect and attraction that I don't know if those feelings can come back, even if he changes.

What makes this even harder is that we both come from cultures where divorce is heavily discouraged. Almost every year I've told him I don't think we're compatible and have wanted to separate. Each time he begs me to stay and promises to change, and because he's genuinely a good person who loves me, I end up staying out of empathy and hope. 

To be honest, I’m not sure if I’m just venting here because I feel frustrated or I actually want to separate because it is hard to simply walk away from someone who I’ve been living with and who does actually love me. 

Has anyone been through something similar? Were you able to rebuild respect and attraction and be in a happy marriage after losing confidence in your partner's judgment, or did you eventually realize that love and kindness alone weren't enough to sustain the marriage?

TLDR: My husband and I are deeply incompatible personality-wise, and looking back, I don't think we would have ended up together if not for the timing of the pandemic. We've now been together for seven years, and I feel like that incompatibility has led to years of frustration, poor decisions, and resentment. My husband is kind and genuinely loves me, and he's finally starting to change through therapy, but I don't know if it's too late or if I've already lost too much respect and trust. I'm not even sure if I'm venting or if I truly want to leave—I just don't know how to think through this situation anymore.