Am i (36 F) ignoring the red flags with him (50 M)?

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I (36 F) have been with my boyfriend (50 M) for around 8 months. He is in his 50s, divorced, has children, and is currently going through a very difficult financial situation.

I love him and I believe he genuinely loves me. This isn't really a question about whether he has feelings for me. My concern is whether he is actually a good long-term partner.

Some examples:

- Last year he needed money urgently for a business matter and I lent him USD 40,000. He told me I would have it back within a week. Shortly afterwards his assets were frozen (this part is true) and he has not yet repaid me. He says he will repay me. What bothers me is that I generally have to ask for updates rather than him proactively giving them.

- i have also lent him money for things like dental treatment when he said he couldn't afford it. Because of his financial situation, I have paid for every date.

- Whenever he goes through stress, he tends to withdraw. He remains active on his phone but communication drops off significantly. Sometimes he disappears for a couple of days without warning. This has happened multiple times, even after I've explained that it hurts me.

- He once told me that after a major business loss he disappeared for months, ignored calls from friends and business partners, and his assistant eventually had to physically track him down.

- He has made a few comments during the relationship that I found surprisingly insensitive, including calling me "retarded" during an argument (he later apologized).

- He once joked about "pushing me down the stairs" if I got pregnant. He later said it was obviously a joke, but it stuck with me.

What is making me question the relationship is that I increasingly feel that when something goes wrong in his life, other people end up absorbing the consequences.

I don't doubt that he loves me. Am I being unfair, or are these legitimate concerns about his character and suitability as a long-term partner?

TL;DR: Boyfriend says he loves me and I believe him. However, I've lent him over $40,000, paid for all our dates, watched him repeatedly withdraw during stress, and increasingly feel that other people absorb the consequences of his problems. I feel loved, but not protected. Am I overthinking this, or are these serious red flags in a long-term partner?