1. Yes this is feasible. The only challenge is that Chipyard's RTL simulations will not capture the functional behavior of the PLL/IOCells/etc, since they all exist outside of chipyard. If you want to perform RTL, post-syn, or post-par simulation of your complete system, you'll have to set that up on your own.
2. Yes. That is correct. uart_tsi sends TSI packets encoded as UART to the FPGA. The FPGA decodes the TSI packets, converts them to TileLink, then sends them as serial-TL to the DUT. In principle, another approach could be to send TSI-encoded-as-UART directly to the chip through a UARTTSI receiver on the chip, bypassing the need for a FPGA entirely. For this to work, the UART on the chip must be running at a known fixed frequency during the entire process. Having a FPGA is also generally useful for bringup, so the no-FPGA-bringup flow hasn't been developed deeply.
-Jerry