[CaberTosser]

TireBobs take hit it pretty well. MY family has done this for three generations that I'm aware of. My Grandpa and his two brothers started a construction business but were working for the family business that they were born into when they started the new venture up. One of them spec-built a home following WWII and he made good money selling it, then he built a second with the same results, then he got his brothers into the fold with him. I suspect some seed money from great grandpa went into that. The 3 brothers business was a great success and they became even more well known in their community than from the preceding family business. When my Dad was positioned as a manager to buy into his employers business here in Calgary there was some family money that helped him do so.

When my sister and I were young adults our Grandmother liked to help out with sensible purchases, she wanted to sponsor mattresses and major appliances. I was renting a suite and using a Laundromat when she made the offer to help with a washer and dryer, being that I wanted to be very respectful of her offer and show some sensible frugality I selected a mismatched laundry pair from a used appliance shop. Grandma was a frugal woman, a daughter of Scottish immigrants she grew up in the Great Depression so that surely accounted for her penny-pinching ways in spite of having become wealthy.

Grandpa's surviving brother is very financially comfortable and he has been generous to his adopted daughter, his surviving biological son though is another matter. The guy is useless and my uncle knows it, but he supports him anyways. He has declared his adopted daughter as his executor (he's 94) and it will be up to her to send the cheques to her useless substance-abusing brother who is living in Vegas. Sometimes the apple falls pretty far from the tree: WWII veteran/ businessman & self-made millionaire/ community philanthropist spawns freeloading junkie. This uncle is a real hoot, he's 94, he day-trades stocks for 6.5 hours a day and continues to make an enviable income. The curious part is that I'm the spitting image of him, so much so that my late Aunt was looking at me rather entranced when we were last together.

Anyways, back from tangentville: there will be people who do deserve generosity and those who don't. There will be those who can get by of their own volition without any financial help and those who can't even make ends meet when the world is handed to them on a platter. If you feel like extending a gift or a loan just be sure its not going to cause you any financial hardship , what if you live 15 years longer than you expect to? As noted already, the experience of a person dealing with a few reasonable chunks of money earlier on can help them from wasting it and regretting their actions were they to receive it all at once.