<human>: Can you succinctly summarize the text in 1-3 sentences?

Me (28F) and my boyfriend (27M) have been in a long-distance relationship for 8 months. During that time, we've visited one another an average of once per month, with me visiting the most. I've been there 6 times, he came to see me twice and we met halfway once, on a trip that he planned with his cousin and later asked me and my friend to join. We live 6 hours away. 

He is self-employed and doesn't have a steady income. Business hasn't been great for the past year or so, and he's doesn't have much money, which is why I would feel bad asking him to visit more. He will hopefully get a teaching position this month, but has debt he needs to pay, so I don't think it will make that much of a difference to me.

I don't know when I'll see him again. I don't know if I should go, wait until he has the money to come, or outright ask him to come (read on to see why). 

I don't mind visiting him more now that money is tight, but here's the thing: he usually goes out with the same group of friends for dinner or drinks about 3 or 4 times a week. I don't know how much he spends, but it seems to me that he could maybe go out a little less so he can set some money aside to come see me.  It saddens me that he's always telling me how broke he is and how much he wishes he could come and then be like "btw, I'm meeting my friends for drinks, see ya!". 

I should mention too that I've offered to pay for his trip, but he's refused every time. I often pick up the tab when we eat out, too. 

On top of everything, my family's been pressuring me A LOT, because my conservative parents think he should be the one to always come visit me, and that I should only go there on special occasions (I don't agree, I think it should ideally be 50/50). They say that him not coming shows a lack of interest in me, so they give me a hard time everytime I tell them I'm going to see him.
<bot>: Boyfriend says he's broke and can't visit me but goes out with friends often. Should I ask him to visit me more? What would be a good way to bring the topic up?