That will make the purchase void and tie up your money for nothing. 

And planning to take rent via cashier check/money order. 

If they do not qualify for conventional loans most private money are business purpose loans and require you to put it into an LLC

I'm not a cashflow is everything guy but I don't like taking money out of my pocket to pay bills. 

You will then have a few options with that rent money....you can put it into principal or you can start saving it to purchase yet another property.

Tenants save money when using a shared meter, so there's plenty of room for error when calculating how to distribute the charges. 

Subject to seems to be more ideal to avoid any confusion over ownership, but it sounds like a pretty involved process that could cost time and money (whereas the other approach is free and simple).Any insights/advice would be appreciated!

To summarize, if you are approached by a syndicator raising money for a multi-family building that meets this multiple offer fact pattern (as is usually the case) who is awarded the contact, they more than likely assumed the most ambitious rent growth, most understated cap ex costs or operating expenses or lastly the cost of equity (your return) is projected to be less than the LP’s the other bidders relied upon.

Real estate investing makes money.

Love the STR arena of investing and providing a place where guests want to pay you their hard-earned money to stay at your place.