They did try to pay the OP back - to me that makes all the difference. To me it is as much situation where an unfortunate family hardship occurred more than blatant reluctance to repay a loan.
Several thoughts aimed at the OP:
Do they blame you for his falling off the roof? consciously or unconsciously?
Do you know that they know you borrowed money to pay for your roof? In other words, have you told them in plain English: “I borrowed $X to pay for my roof after lending you the money I had earmarked for the roof. My monthly payment is $Y, each and every month. And I’m making those payments by not eating out, skipping lunch every other day, no new clothes, etc.”
Have you told her in plain English: “Every time you go out to eat you prove you could have paid that money back to me instead. But you don’t. That feels like theft to me.”
Bottom line:
It’s very easy for them to persuade themselves that they need that money more than you do. It certainly sounds like their middle-class expectations world is collapsing around their ears. It’s especially easy for them to persuade themselves if, like most folks, you don’t talk about money at all. It’s harder for them to do that if you’ve made your situation and POV 100% crystal clear to them. Namely that your comfortable middle-class existence is also collapsing around your ears.
Harder isn’t impossible though. They may well simply be flakes and you may well be happier to abandon any recovery efforts or expectations. I for one would not do that until I had a straightforward, calm, deliberate, and very heartfelt talk with them.
My bet now is that you’re guessing at what they think or know. Stop the guessing. Plain English is an awesome tool. Use it.
Not that I’m saying you should do this, but if you’re really hard up for money, you could possibly get a tax break by writing off the loan and reporting it to the IRS. Of course, that makes your sister liable for income taxes on the amount forgiven, and that probably makes for an awkward family situation.
The broken hip didn’t keep the BIL from working in the restaurant, because they basically bought it for one of their kids, a layabout who’s never really worked a full week in her life. Since she wasn’t college-bound (they helped their other 3 daughters through college), the idea was they’d buy the restaurant so she and her boyfriend could have a business and a place to life (apartment above the restaurant). It didn’t work out that way.
They’re aware that I’m paying off a loan borrowed because they haven’t paid me. They’re aware I"m paying interest on their debt. Part of my issue is not only their spending, but the fact that the BIL (who is at least more concerned about the debt than my sister) keeps dreaming these pie-in-the-sky dreams about how he’s going to augment his retirement income with little work on his part. “Oh, I’ll buy a farm and cut hay. 6 weeks of work per year and it’ll be great!” (They didn’t buy the farm) When I told him my retirement plan was to work hard, live frugally and save a lot, his response was, “But wouldn’t it be nice not to have to do that?” Sure, but not realistic.
I can afford to pay this off. It’ll be done soon anyway. But I’m by nature a strong ISTJ. I plan, I execute. I don’t know that even if I “forgive” the debt I’ll be able to forgive my sister for not following through with her word.
StG
This would piss me off - but what can you do?
If he thinks getting some extra income by making hay is opting for the easy life, he’s damned near certifiable.
saje - He thinks it’ll be hard work for the weeks of baling/stacking, but easy because he thinks the hay just grows itself. When I told him that my hay guy routinely seeds and fertilizes his hay fields, he sort of shrugged that off. And he thinks he can hire $10/hr high school kids to do the heavy lifting. Not as easy as it sounds.
StG
I think the part that would get under my skin the most is that they’ve freakin’ retired way early, while blowing you off. They couldn’t have worked a few months longer in order to pay you off? Sheesh.
In retrospect, why didn’t she borrow the money for the restaurant from a bank?
yeah, write it off. I (personally) would also probably stop speaking with them. If they want to make it right, let them come to you.
and if they hit you up for another loan (since they sound clueless enough to do so) then you can rip into them.
As a lifelong horse owner, I shudder at the thought of making a living growing hay…
You have no choice but to forgive it; she’s not going to give it back. What are you going to do, sue your sister? I’d also forgive her rather than be angry with her forever. It’s a shitty thing your sister did, and I’d be pissed too (I’ve been in this situation, and I was pissed), but at some point you have to make the decision to not be angry. Yes, it rankled me when my brother posted Facebook photos of his vacation (is he kidding me?) while owing me money, but I’ve put it behind me. I’ve mainly forgotten about it, and only remember when the topic of loaning to family members come up.
From now on, don’t do it. And if you do, just know it’s a gift. Don’t even expect it back, regardless of if you’ve expressed that it’s a loan. It’s one of those life lessons.
Think of it as tuition. You learned some valuable lessons about your family members and henceforth that knowledge will serve you well. I had a similar situation with 3 family members. Years later, long after I’d quit caring, they pressed the money on me - they wanted to square their debts.
This occurred to me also. I know the OP said that the point wasn’t for the BIL to work in the restaurant in the first place. But there’s been a lot of talk about how the sister/BIL thought they would have more money, thought things would go differently, etc. Well, I’m guessing they didn’t really plan for a broken hip. A broken hip is no joke, and neither are medical bills. Not saying that’s an excuse per se, but perhaps a reason why finances are not quite what they thought they would be.
Apart from that, what everyone else said: Don’t loan money to friends or family. Give money or don’t give money, but don’t loan. Since the damage is already done, cut your losses and write it off if you care at all about your relationship with your sister.
They didn’t incur any medical bills, he went to the VA.
So, I talked to BIL. Instead of couching this as a collection call, I explained that having having this out there was making me feel angry, which I didn’t like. He said part of the reason they weren’t repaying me is that they sent money to my brother, the cancer guy. (one of my other sisters has sent him $4000, too). He volunteered that since some things have changed recently he’ll begin paying in July. He says $1000/mo. I told him that would be great, but to make sure whatever he promises is a doable amount. Better to under-promise and over-perform. We’ll see.
StG
I hope it works out for you but my gut feeling is that you should just forgive the loan right now and put it behind you.
Anyway, good luck.
I’m gonna take a different course than most people who would probably tell you your sister is a scumbag and you should disown her.
Is $10,000 really worth losing a sibling over? She might be kind of a crummy person, but let’s put it this way - you’re never going to get another sibling. Ever.
Just devil’s advocate/food for thought. Not judging you 
Good luck!
Most people would say that? Doesn’t seem like that’s the case here, where most responses are “forgive and let it go.” Frankly, I was surprised at how unbalanced it the responses were. I figured on a lot of “let it gos,” but not this percentage.
Not about this case, but that’s terrible to me. Blood alone is a horrible reason to keep the peace or keep someone in your life. I’m a strong proponent of cutting ties with people who treat you badly. Blood does not, and should not, grant license for one person to allow another to treat them like crap.
Yeah I’m actually pleasantly surprised how many people are suggesting forgiveness, being this forum tends to be very pro tough justice and hardass in general. I would have expected a chorus of “kick her to the curb”.
Silly as it may sound, you might try making a Pros/Cons list. You may have to start a few of them as you narrow down the real options and your own take on it. I’ve done this before and gotten–maybe not exactly from the list itself–a lot of real insight into how I felt about something.
Good luck–this is a tough one.