Would I be better suited trying to find a Fix N Flip, pay cash using my equity, do the work myself and then put it back up on the market or would I be better off purchasing an STR with 20% down and leveraging a loan to get some cash flow coming in then maybe pursue a Fix n Flip using the remaining equity and let the STR repay the HELOC until I sell the flip?

I lived in N Charleston for 9 years while I was in the Navy. 

What part of N CHS is it in?

They need to be around 60 cents on the dollar ARV.Go to local investor/BP meetups and network with buyers of W.S. properties, these are typically Fix N Flipper's, Local Contractors, or just a buy and hold investor looking for a great deal that they can reno and keep.If you don't want to deal with the dispo portion of it at all, you can network with other investors that focus specifically on the Dispo.

I'm here following my passion n dreams of buying and investing in rentals.

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@Julie N. - Thanks for the feedback. 

Heck, I'd maybe get to a place of all but requiring some such basic competency completed before I take on a buyer client because I too get exhausted of answering the same basics and directing over n over to get with CPA to go over details. 

Fix n flip. 

A fix n flip type loan may be the "easiest" but a conventional loan will still be cheaper.