Looking from the outside in, what mostly concerns me about NYC is the strict landlord regulations, high taxes, etc. 

From a strictly numbers standpoint, if you could save up the money needed to put 20% down on a property, then a conventional mortgage makes more sense for you. 0% down VA sounds appealing, but the issue with this is the VA funding fee.

I guess I kinda learned that the 2% was a very strict rule of thumb that isn't a clear cut buy/dont buy signal.

Look for properties where there is not so strict Lanldord/Tenant laws.

Depending on how strict your building department is, a simple Matterport floor plan which will cost you under $500 should do the trick to highlight all of those items and assist with planning. 

I just purchased a 3-unit apartment building in East Orange and I am looking for a go-to handyman to handle routine repair work.

Strict “default schedules”, etched in stone date nights with both the wife and kids, plan the day trips, soccer games etc, out in advance...I agree time is more valuable than money and as I have scaled I have allowed lower returns in return for time - which has allowed me to scale.

On some, you would need to register as a business, on others, it's in strict violation.There are plenty of free platforms out there that are built around rent collection.

@Michael BakerHi Michael,I have decided that a duplex is the best move.I have a max purchase price limit that I wont go above or I won’t have enough money to finish the process.There are duplexes available at or under my max number in my area.Basically I have budgeted to hold for 2 months while we renovate.10% down is what I am planning to put down.Then I have enough left for reserves, closing and all the other costs associated with closing the deal.It would have a low cash flow if I treated it strictly as a rental (at least at the beginning).I have some plans to increase the income on the property that will allow me to cash flow better within a year of buying it.

I was strictly interested in cash flow only.