I understand there are rules in place regarding STRs, so I'd like to find a realtor that is familiar with the rules, codes and laws that can guide me.

There's been talk of how these will intersect and it's already happening in some spaces and I'm not talking about Metaverse Real Estate (Although I think some of that will make some people VERY wealthy).I'm talking about real physical real estate providing access to crypto investing and returns, and here's the crazy part...It has the potential to offer all the great things real estate does like depreciation, hedge against inflation and cash flow, all while exposing you to the high reward of Bitcoin's upside and decentralized nature. 

I'd focus on the ROI of "doing some updates" and the strategy behind this property.

I'd like to see how this plays out.

I’d take it to $1500 and assess again next year. 

I'd get on some off-market lists, but avoid those areas(NE Durham, most of 27610 just south of the ITB, etc.).

Although HELOCs are generally more challenging for investment properties and might come with higher interest rates, it's not impossible to find one with effort.I have a VA lending contact who is a retired Army veteran himself.

I'd sell it especially as it has a large lot and a pool (while some tenants love the space and pool, many are not prepared to take care of it). 

Liquidity is important in the flipping business, so I'd hang to as much cash as possible. 1 thing to note;Those who can, do.

Here's what I'd want to do either way: I want to install security cameras on each property I buy and put them on a sim card plan so I can view my properties at any time.