I utilized (and maxed out) my credit cards to afford the materials necessary to renovate the apartments (I know bad move) therefore I cannot acquire a loan of any sort to fund the initial funds necessary to acquire a hard money or DSCR or rehab loan.

Now the city initially said they would limit the amount of days, but upon going down there and spending time with the city workers there (they are very nice) it seems there won't be enforcement on the number of nights rented out.

This could also open the doors to direct equity investments in the future if you scale and continue to hold these initial assets.

Initially we had intended on starting our real estate journey through multi-family house hacking, but this opportunity popped up first and it was hard to ignore.

S8 Challenges:1) Voucher holders not having funds for application fees or security deposits2) Tenants trashing properties, killing ROI3) Tenants not paying their portion of rent or utilities4) Tenants not cooperating with ongoing S8 requirements or inspectionsAlso, you stated in your initial post that you'd be buying turnkey rentals.

Initially I was planning to use a mix of cash and stocks to fund this purchase, but now having the second thoughts whether I should use  just some cash and apply to some home equity financing options instead to cover the offer amount. 

That is my initial impression, but I am not an expert.

I was initially going to put down 10%-15% but the new lending requirements only required 5% down- allowing me to keep additional capital for reserves.How did you add value to the deal?

If the market goes well, they can 5X the initial investment, take 30% carried interest spread on $50M, and buy a ton of luxury real estate to take even cooler pictures of their life on Instagram. 2) Extreme diversification, sprawling, "strategy and synergy free" portfolios:The other take that is possible from naive social media followers, but not from sophisticated family offices or private equity shops is one where a syndicator raises a ton of money across multiple different types of asset classes in a seemingly random set of geographies. 

If you can hold onto the property for more than 5 years, the potential for appreciation and equity growth could offset the initial negative cash flow.