When in Due Diligence have a thorough inspection and get estimates for any work that is needed now and potentially in the next 3-5 years. don't forget about the tax benefits to doing the work upfront.

I feel I'm finally ready to spearhead my own project.

The homeowner has direct title, can sell at any time and gets 100% of the appreciation and tax benefits on these houses.

He isn't a motivated seller.If it will rent for $1900  a month, that means to make money you have to have a payment that includes, principal, interest, prop taxes, insurance, at less than $1400 a month. $190,000 at 3% interest is P&I $801 + prop tax plus insurance a month.

NC is a great market for your goals, however it will be challenging to find inventory that has much cash flow; many people who toss money into multifamily here do it to avoid the tax bill + take the 10 year runway of growth.How much SHF RE do you currently have?

If you did a full repipe and gutted the entire property then I assume (in all that means) that there were permits pulled and this should have been caught when the inspector did their rough in walk through or atleast the final occupancy inspection. 

After collecting tenant pass-throughs for the year, do you pay the property taxes at the end of the year or the beginning of the next year?

Once the work is complete, inspections from the DOB and DOT will finalize the process.

If the signs point to selling, consult your CPA about the tax implications.

Real estate investing has been a passion of mine for time with my mother also having invested early on where I likely have gotten the love and desire to follow similar foot steps.I have taken last 6 months to educate myself and currently own a single family home as primary residence and would like to expand to multi family properties (2-4 units) for additional stream of income, not to mention potential tax benefits for long-term investing.Based on current living situation, I have a fair amount of equity established in my primary residency along with having enough cash to either pay off house completely or use towards investing in a multi family property.Given that I'm the sole source of income for our household with my wife being the home maker for our two kids under 2, trying to weigh out risks with getting started now or perhaps waiting.