As mentioned above it depends on your goals as well as what each options provides you. 

For smaller deals like owner finance options, it's important to build a strong relationship with the seller, as this often leads to more flexible terms.

I will ask again regarding pipe lining options.

@Collin StewartSince you're PCSing to Columbia, SC, and have VA loan entitlement remaining, house hacking a small multifamily with a VA loan is a strong option since it requires zero down.

Being a NYC resident (originally from Long Island), the price of entry in the area is on the higher end, so I've been considering some options in the NY Capitol region, as well as NJ and CT.

Read my Utilities 101 below to see some options.

If you can make a conventional loan work, it’s likely a better option.

However, there are better options than $180 a month and $1000 for a WP site. 

Plus, many of the properties here are older and not exactly cheap.My other option is Tucson, AZ, where I’m originally from.

Also, after a year, the mortgage hasn't been paid down by much, especially if it's a 30 year mortgage.The only challenge you may run into is if you purchased it using a low or no money down mortgage option like FHA or VA lending.