We were interested in rolling money from a sale of a triplex into a larger property.

I Brrrr-Ed it and have already gotten all my money back out.

Comparatively, you can get a lot more for your money in Omaha compared to Boston, but way less potential scale as well.

They have custodians that manage their money, and you are simply the beneficiary of that account.

🙏🏼 You can pickup a Section 8 house in Cleveland using your money as the down payment.

@David Martoyan, the deal you feel you "need" to do is the deal you will likely lose money on.  

Why would you be going hard money and not conventionally financed?

If you can live for free and only pay utilities AND buy an investment property, that would be ideal in terms of savings and cash flow.If you can't stay and your parents want to make some money on that property, then yes, house hacking would be your best option especially since you don't want the best place in the multi.

Have you looked into becoming a private money lender to put your money to work while you wait for your next purchase?

Depository institutions are highly regulated in the risk they bear because they lend out their depositors' money.