Since then I have been working a job I enjoy and contemplating getting back into school to continue down that road for my BM degree and not too long ago I was listening to Grant Cardone talk about building wealth and he said something I will never forget:"Make it a rule that you never use debt that won’t make you money."

One stole a vehicle to go to court in another state, one was selling meth, and the last one sexually assaulted an old lady in an alzheimer's ward. 

why not just tell him the problem, and see what he wants to do to fix it. after all, it is his house, as a result, his decision ultimately......why he's contemplating everything, make the suggestion, and offer to eat some of it (awfully generous of you) if he uses your brother?

I always suggest that individuals contemplating real estate investments 'do the math' to determine the initial total cost of acquisition (year 1) and ongoing income/expenses including maintaining a cushion for any unanticipated expenses.  

@Brandon Turner will be happy to hear you are contemplating a "house hack"

I am contemplating renting my house or lease option on it. 

IF it's on a concrete pad, natural gas fire pit and direct hook up for the BBQ, then it's probably not going to be an issue.John, since you are starting from scratch, as long as this is contemplated while designing it, you are good to go. 

I advised her to vet those then and get back to me should they not work out... but it left me contemplating my dilemma so that even without being the highest I could be strongest. 

I am contemplating getting into Real Estate Investing.

I'm contemplating visiting the address noted on the property record, and perhaps talking to the neighbors there to see if they know how to get in contact with the owner.