Should I approach wealthy sibling for private financing?

[Myles M.]

We're looking to purchase foreclosed, REO properties but most of these deals go to all cash buyers. We have a team in place - trusted contractor team, experienced and handy landlords (us, LOL), good credit. We've lived in our target area for years and know it well. But we don't have the cash to close these deals.

I know the mantra in real estate investing is to make money when you buy, not when you sell. The last property we bought was a conventional purchase at full retail value. We knew less then, and we won't make that mistake again. 

Every one of our friends who purchased off market/undervalued deals did it with family assistance. Every single one. They were able to snag undervalued properties in the most expensive cities/states: NYC, CA, and HI. 

I have two siblings, and one of them is extremely wealthy. We are fairly close. They built a multimillion business from the ground up and have a fairly diverse portfolio. I've thought about approaching them to ask for the upfront capital to get us our first flip/rehab deal, but I haven't yet for a number of reasons. They know we've been trying to buy. 

I don't want to risk souring our relationship if I make an ask. Beyond that, would would motivate someone who is already extremely wealthy (other than kindness)?  What would you advise? 

[Diane G.]

Myles M.
Yes, 99% chance this is a bad idea...

One thing you said strike me as really odd is that everyone you know has family assistance.... then you are probably hanging around the wrong crowd.... everyone that I know do not have family assistance.... seriously....

Plus someone that succeeds on his/her own have the tendency to resent people who would ask for help becasue that is not how they made their money , and so they don't believe in it...