Buy at 3k for local support/take home no issues with transit etc..price match and send it documentation to get it down to the 1800.Take it step further...lease new car vs buying one (even old). 

Too add, it's a block away from NJ transit into the City and next year a ferry service opens up in town.

Do I want to build a working relationship and transition into bigger deals down the road and use these smaller ones to test out the waters?

Well a partner and I are looking to turn one of his properties into a transitional home to help the alcohol and drug abuse its a 4 bedroom and 1 1/2 bath I have no idea!

I am currently active duty in the USMC but will be transitioning out within the next several months.

I've personally found that the learning curve is much shorter as a new investor, if you are willing to put in the work to understand your local laws and tenant/landlord rights yourself and manage your first few properties yourself, before transitioning to a property management company.

It will be better for you as you transition from an assistant to an agent down the road. 

I have a connection that will allow me to smoothly transition into being a broker after 2 years (about a year after I graduate).

How many investors actually convert and make this transition in the investing carriers?

I’ve been using 2 year leases and have been transitioning to one year leases.