I have a US Cutter Laserpoint I use for basic designs, lettering and numbers ,Heat Transfer and Stickers. It is a great little machine for very little cost. I also have a Roland GX-24 as well.
I bought the US CUTTER first and it paid for itself in the matter of 2 months. Tshirts are easy to make and got in tight with a few Adult softball leagues and soccer leagues and now have about $200-$300 of monthly business just from those leagues and referrals.
If you want basic software for free and good ideas on basic designs got to cadworxlive.com
Joining is free and everything is stored on the web. easy to use and you can import designs and cut them thru their site. Its a great service from a company you can buy supplies through ( but dont have to buy, this is a free service they provide)
Buy what you can afford and get cutting. Upgrade if you want and as you get busier.