My goal is to hold on to this property for the long haul.

My main goal with BiggerPockets is to connect with other investors and hopefully build a reliable network of lenders, property managers, contractors, and agents.

Where you pick will depend on your goals for cash flow and your budget to buy.

It seems like you have some very solid goals of multiple income streams, and a well calibrated risk tolerance. 

Depends on what your goals are. 1-4 units are still residential, so it doesn't really matter how you start.

@Yamil NafRaising $160,000 for your short-term rental (STR) venture is a great goal, and there are several ways to structure the deal to minimize your upfront costs while attracting investors.

My long-term goal to continue aquiring properties.

My ultimate goal is to house-hack this deal as well. 

Are there any creative things that could be done to get to my goals or from your standpoint,  or is it pretty well a firm "not gonna fly" type scenario? 

Overcoming Common Financing HurdlesMortgage brokers excel at tackling challenges that often derail new investors:Low Down Payments: Brokers can find lenders offering low or no-down-payment loans, ideal for new investors with limited capital.Complex Income Streams: If you’re self-employed or have variable income, brokers can identify lenders that accept alternative documentation.Competitive Rates: Brokers have the leverage to negotiate better rates and fees, saving you thousands over the life of your loan.Pro Tip: Communicate your investment goals clearly with your broker so they can tailor their search to your needs, whether it’s a short-term fix-and-flip loan or a long-term rental property mortgage.3.