We are able to borrow the money at 5%, however the lender also wants a small portion of cashflow (not equity) from each property we buy.

I think it becomes hard because of the unknown variables of time toward money output and also keeping up with the laws as they are constantly changing.

Exercising may cost a little money, but it places you in a much safer position.

I've dabbled in the new construction space here in Chicago and there is A LOT that goes into it...I'd highly suggest spending some 1:1 time networking with some other investors like @Jennie Berger or @Prashanth Mahakali who are both Chicago developersYou make your money with the land purchase and then systems/processes/volume over time in the development game, but it's not easy and competition is high!

I just want enough money to travel the world and give back to causes I care for. 

Oakland is not a hands off market, but done right can make money.

Friends and family is where I started looking for private money, as there was already a trust factor there.

Conversely, I also know people who find communicating with guests and cleaners to be incredibly draining, they don't know the first thing about managing an STR nor does it particularly interest them, and they would rather spend their time making money in their main job rather than taking on a side hustle that they may not be able to do as effectively.

She then tells me that she can’t come up with the money for a deposit.

We make more money on nasty value add properties.