Long-term rentals offer diversification, learning experience, and lower returns but may generate lower returns.

My initial thought is this could be a money maker for MF owners.. 

Purchase price: $500,000 Cash invested: $100,000 Buy and hold multi-family property initially house-hacked prior to purchasing the single family in the burbs.

I’m also currently looking to upgrade to a software that allows me to transfer friends from PM to owner and will help me generate form 1099at the end of the year.

PROGRAM 2 Owner use up to 3 weeks 40% of Adjusted Gross Standard FF&E in high season & 3 weeks Revenues from the Unit and accessory in low season package required.PROGRAM 3 Owner use up to 6 weeks 30% of Adjusted Gross Standard FF&E in high season & 6 weeks Revenues from the Unit and accessory in low season package required.HIGH SEASON: DECEMBER 21st - APRIL 15th LOW SEASON: APRIL 16th - DECEMBER 20thNote: The following fees are deducted from the gross revenue before the split:5% Management fee, 5% Travel Agent Commissions, 2% Credit Card Commissions, $4.00 per occupiedroom night (TRUMP Fee) & Group meeting fee may apply.Other Monthly Fees: 4% of the gross revenue is moved to the FF&E Reserve account and approximately$20 for liability insurance.Monthly Condominium Dues: $895.57 (These can be deducted from your monthly revenue)Initial Rental Program enrollment fee $500 and $2500 initial FF&E Reserve account contribution.Fees for OWNERS STAYS: In Rental Program (Optional): 1

In turn, this makes me a big fan of HELCOs, but still, that initial investment is going to be a tough one.

That leasing agent can provide very good insight into what is moving in the market and how to generate more income. 

Ideally, I would love to buy a multi-family property and rent it out, I would consider house hacking but I mainly want to my first property to be one that I can improve on and have it generate income for me.

Assuming you're in the Charlotte market, there should be plenty of room to generate cash flow and subsidize your new primary mortgage. 

Short-term rentals are booming right now and offer a great way to generate income quickly.The key is to take that first step, do your research, and believe in your ability to make it work.