In this area, people usually rent for 1-12 months, and the rent is 30-50% higher than unfurnished LTR.

I would just use rentredi to screen tenants and collect rent payments. 

Local market rents are between $1400 and $1900 /mo within 2 mile radius.Two of the homes are 3 bed, 1 bath, appx 1230 sq ft, same rents as above.Each home is worth appx $265,000.

You most definitely can go in on a Fourplex with 3.5% down, primary residence, living in one of the units, find out what purchase power you have, and what the rent rolls for the other units will be to determine your cash flow. 

I'm currently house hacking a property in Raeford and plan on renting it out.

About 9 months ago.The property was a primary residence of the first owner until shortly before passing, after this it has always been rented out.No depreciation was ever claimed by any owner at any point.Tax implicationsAs I understand it:A.

Or is it more advantageous to keep renting and buy an investment property to rent out instead?

so If it rents for $3,000 I take 30% of that out for taxes, insurance, maintenance, etc. 

I rent multiple rooms, farmland and shop space.

I am now summarizing the key points for managing rental properties to build my systems before launch ( I am strongly considering Rent-Redi software) but I am wondering how I would use this software for client's properties when collecting rent, holding deposits and the like.