One of my colleagues house hacks himself, and I plan on doing it as well once I can get the cash to put money down!

It was our fault so it is what it is, but it sucks that an honest mistake that would have been a super tiny inconvenience for the guest ended up being a huge thing for us with a monetary fine and likely lots of money lost in future reservations.  

I was thinking of doing some creative finance: Maybe offering to take all three properties off of their hands with a lease to own, so I don't tie up all my money.

So I'm coming up with ideas of how I can make money wholesaling and I have some questions to see if these ideas could work.If i were to go under contract with a FSBO, for a set price on a property with an assignable contract.

Another consideration is that he may be retiring soon so do we need to make the purchase before he retires because DTI will come into play? 

Unless you have a vast network/sphere of influence to keep you afloat, making money being an agent can be really tough and you can literally go months without a paycheck.If you want to be licensed and learn it while you have a W2 job that's different.  

My brother and I want to get into real estate investing for passive income, and we’re thinking about starting off with a duplex in a year or two after saving some money, that we can live in and rent other unit(s). 

You could be on the hook for a lot of money.

Alternatively, they can sign a new lease and save a lot of money.

I don’t use every feature, but it definitely frees up time for doing more money making tasks!