Under the "Howey Test", a transaction is an investment contract if: It is an investment of moneyThere is an expectation of profits from the investmentThe investment of money is in a common enterpriseAny profit comes from the efforts of a promoter or third partyIn other words, if you are putting together a deal in which people are investing their money (rather than donations, or contributions to a charity), and the money is "pooled", and the only way your investors make money is from what you do as the "Promoter"/Deal Maker/"Sponsor", than it probably is a security, and it probably needs to be registered (at the state, and possibly Federal) level.On the other hand, if you are getting a group of people together, and your are jointly putting in money, and "other services", and equally sharing in decision making (so it's not "all on you) then it may not be a Security, but is more than likely, a Partnership.  

Probably would require a transfer of ownership interest of the house to the sibling (or sibling's LLC or entity) before that sibling's interest is sold to the other sibling.Donating a portion to charity might avoid capital gains, but specifics, methods, and timing matter. 2.

So it sounds like it was really just a charity endeavor the past decade, because even if you collected expenses and never did a repair (who paid for the roof?)

You're not running a charity or a halfway house. 

@Charity Crowley I had someone else’s I helped do the same and 4 days later they had a payment schedule but the status at the top Stayed the same 

Aloha,You are just asking for headaches...or are you planning to run a charity?

It's nice to know there are charity landlords that aren't running a business.

In fact, either one involves humans, so any of the above are possible, along with kindness, charity, community, honesty, caring, motivation, creativity, generosity, compassion, family and love.Hopefully, a hybrid or evolutionary combination of beliefs and practices will bring the human race to a higher level of enlightenment, as long as we don't get so outraged at those that don't share our perceptions or beliefs, that we destroy each other first.

Though they are then making you operate as a charity for charging less.) they should stay.

Thats when I was doing consulting for our Charity so that was a great donation she made and I was proud to help her through it.. win win for all.