Just got off phone with brother. It was surprisingly painless and he even thanked me for helping in the past. He also said my dad might help him out. Thanks again for your advice all, it was truly helpful.

I'm glad I posted here, reading your responses has helped me develop my view on a few of things:

1. Although the money is inherited it was still worked hard for. I am to use it as responsibly as if I had earned it myself. Someone else did indeed work hard for it and then trusted me to use it responsibly. Of course helping those I love could be considered responsible usage, which leads me to...

2. Is brother in need? I don't know this for sure. I'm not sure how much of his inheritance he has spent - however there are several annual distributions (from a trust) which he will receive for the rest of his life. I believe he can make it work, and this loan is just to keep him a little more comfy. I am speculating a little bit here but I think he has a parachute if he really (really) needs it. After reading your responses and thinking it over I'm more inclined to let him get uncomfortable, but I'm ready to help him when he is in "actual" need (not sure what that would look like at the moment - but fairly certain it's not now.).

3. What is most beneficial for everyone? Even if I were thinking what is most beneficial for myself only that would include my brother being happy and financially stable. This loan would be more of temporary pain relief. He still needs to find a way to make a living and of course a loan does in no way accomplish that.

I have't taken my other siblings into consideration at all because what they do with their own money is their business. They may be making a better decision than I am by not loaning him a dime, maybe I'm just acting as the enabler.

Sorry I keep dropping new info about the situation with my posts. It's a complicated situation as you can imagine and also very personal.

So, I'm leaning towards declining to help him now (This discussion has changed my mind!). Open to hear more thoughts, so far your responses have been very helpful to me!

Wow, thank you so much for your thoughtful responses. A few things jump out at me:

First I'd like to respond to BitterCrank since you asked a direct question. The loan was never intended to be a gift, and it was always clear that he would (supposedly) repay me.

1. As far as "investments", I'm about 50% sure I'm never getting this money back. I'm not trying to help him keep his business afloat (he has already resolved to close shop, but he still needs to pay rent for the remainder of his lease). But this would be more of an investment in my relationship with him. That being said, I don't want to be taken advantage of just because I love my brother.

2. I honestly don't want to give him advice. This is for a couple reasons. First, I don't know a single thing about financial planning. I just happen to live frugally and it has worked out for me. On top of that, he has what I would like to call "big brother syndrome". He likes to give me advice (ironic), but he's not so big on the listening.

My other siblings have not helped at all and there is a bit of sourness between them. In fact there is a big rift in my family now due to "who got what" when my grandfather passed away. I don't want that to spread to me and my brother too.

The heart of my conflict is this:
-Don't loan him money: risk him being (unjustly?) angry with me.
-Do loan him money: probably never get it back and feel a bit taken advantage of.

Thanks again, I really appreciate you guys helping me think this through.