Had the same problem, apparently that was because I tried to install Tizen 5.0 which was not compatible with the wearable I tried to install on (should have opened a Tizen 4.0 project in visual studio).
After that I was able to install by running:
$ sdb install <path-to-tpk>.tizen.example.SensiboTizenWearable-1.0.0.tpk
See this example:
C:\tizenSdk\tools>sdb install C:\Users\aviad\source\repos\SensiboTizenWearable\SensiboTizenWearable\bin\Debug\tizen40\org.tizen.example.SensiboTizenWearable-1.0.0.tpk
WARNING: Your data are to be sent over an unencrypted connection and could be read by others.
pushed org.tizen.example.SensiboTizenWearable-1.0.0.tpk 100% 618KB 0KB/s
1 file(s) pushed. 0 file(s) skipped.
C:\Users\aviad\source\repos\SensiboTizenWearable\SensiboTizenWearable\bin\Debug\tizen40\org.tizen.example.SensiboTizenWearable-1.0.0.tpk 967KB/s (633407 bytes in 0.639s)
path is /home/owner/share/tmp/sdk_tools/org.tizen.example.SensiboTizenWearable-1.0.0.tpk
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[start] val[install]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[9]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[12]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[15]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[18]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[21]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[25]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[28]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[31]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[34]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[37]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[40]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[43]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[46]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[50]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[53]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[56]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[59]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[62]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[65]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[68]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[71]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[75]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[78]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[81]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[84]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[87]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[90]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[93]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[96]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[install_percent] val[100]
__return_cb req_id[1] pkg_type[tpk] pkgid[org.tizen.example.SensiboTizenWearable] key[end] val[ok]
spend time for pkgcmd is [27655]ms