Real-time optical OFDM (OOFDM) transceivers with on-line software-controllable channel reconfigurability and transmission performance adaptability are experimentally demonstrated, for the first time, utilizing Hilbert-pair-based 32-tap digital orthogonal filters implemented in FPGAs. By making use of an 8-bit DAC/ADC operating at 2GS/s, an oversampling factor of 2 and an EML intensity modulator, the demonstrated RF conversion-free transceiver supports end-to-end real-time simultaneous adaptive transmissions, within a 1GHz signal spectrum region, of a 2.03Gb/s in-phase OOFDM channel and a 1.41Gb/s quadrature-phase OOFDM channel over a 25km SSMF IMDD system. In addition, detailed experimental explorations are also undertaken of key physical mechanisms limiting the maximum achievable transmission performance, impacts of transceiver's channel multiplexing/demultiplexing operations on the system BER performance, and the feasibility of utilizing adaptive modulation to combat impairments associated with low-complexity digital filter designs. Furthermore, experimental results indicate that the transceiver incorporating a fixed digital orthogonal filter DSP architecture can be made transparent to various signal modulation formats up to 64-QAM.