The property is no slouch, but it could be improved.

The zoning city inspectors were very responsive and glad we were improving building but they wanted the entire building renovated before a single unit could be rented (which makes sense, but my original plan was to renovate 2 units and then market and rent those 1/2 way through to start getting cash flow sooner while finished the last 2 units).

You have at least 6 mos, often more, to find a new OZ property to purchase/substantially improve. 

I do Home improvement for sometime now however I am looking into growing my business in doing flips.

They are also members of NARPM which means they pay to be around other great PMs nationwide and gain/share knowledge to help improve our industry.

Lastly, another way is to look at the areas that have already had improvements made to them.

If not, you should focus on developing some expertises that will be of use to real estate investors and improving them.  

I have made previous improvements while living there over the years totalling $21,000 in CapEx and repairs since 2013.I have two options I see and I am trying to figure out which would give me the best start on building my property investment business.

Looks like you are set up to increase cash flow and with just time and slight improvements over time.  

@David Sisson When I’m presented with a somewhat frivolous request for an improved article when the existing article is properly functional, I either decline or I say that I can bring in a new one, but doing so would require a rise in the rent.