I want to take advantage of the money on the table.

Closing one deal over multiple deals in a competitive environment can provide some advantages. 

I had 2 female roommates Feb-May and I was living for free.

My market is hot, but I’ve still been able to source some things that for various reasons have either sat a while or I was just able to utilize negotiation and holding firm on what price I was willing to go to to work to my advantage.

The only advantage I could see to doing individual leases is if you get higher rents.  

Take advantage of the networking opportunities that @Abel Curiel mentioned. 

I have an LLC, silent partner, one home and am ready to get rolling on more purchases but want to take as many preparation steps as possible when it comes to finances and taking advantages of tax breaks. 

Don't do a HELOC for long term just to have the tenant pay it off, that loses the advantages of HELOCs -fast cash, available any time, but floating/higher interest rates- Also, most won't give you a HELOC on a non-owner-occupied home.

The chances of you knowing your market better than one in a different state is going to be a competitive advantage.

If it is a number of unit goal multifamily can provide an advantage by gaining more units through fewer acquisitions and closes.