So it actually did started then crashed because the following
"17:39:15] [KCauldron version retrievier/INFO]: I/O exception (org.apache.http.NoHttpResponseException) caught when processing request to {s}->
https://prok.pw:443: The target server failed to respond
[17:39:15] [KCauldron version retrievier/INFO]: Retrying request to {s}->
https://prok.pw:443
[17:39:15] [KCauldron version retrievier/INFO]: I/O exception (org.apache.http.NoHttpResponseException) caught when processing request to {s}->
https://prok.pw:443: The target server failed to respond
[17:39:15] [KCauldron version retrievier/INFO]: Retrying request to {s}->
https://prok.pw:443
[17:39:16] [KCauldron version retrievier/INFO]: I/O exception (org.apache.http.NoHttpResponseException) caught when processing request to {s}->
https://prok.pw:443: The target server failed to respond
[17:39:16] [KCauldron version retrievier/INFO]: Retrying request to {s}->
https://prok.pw:443
[17:39:16] [KCauldron version retrievier/WARN]: Error occured during retriving version
java.lang.Throwable
at kcauldron.KLog.log(KLog.java:30) [KLog.class:1.7.10-1420.120]
at kcauldron.KLog.warning(KLog.java:41) [KLog.class:1.7.10-1420.120]
at kcauldron.updater.KVersionRetriever.uncaughtException(KVersionRetriever.java:102) [KVersionRetriever.class:1.7.10-1420.120]
at kcauldron.updater.KVersionRetriever.check(KVersionRetriever.java:96) [KVersionRetriever.class:1.7.10-1420.120]
at kcauldron.updater.KVersionRetriever.run(KVersionRetriever.java:59) [KVersionRetriever.class:1.7.10-1420.120]
at java.lang.Thread.run(Unknown Source) [?:1.7.0_71]
Caused by: org.apache.http.NoHttpResponseException: prok.pw:443 failed to respond
at org.apache.http.impl.conn.DefaultHttpResponseParser.parseHead(DefaultHttpResponseParser.java:143) ~[DefaultHttpResponseParser.class:1.7.10-1420.120]
at org.apache.http.impl.conn.DefaultHttpResponseParser.parseHead(DefaultHttpResponseParser.java:57) ~[DefaultHttpResponseParser.class:1.7.10-1420.120]
at org.apache.http.impl.io.AbstractMessageParser.parse(AbstractMessageParser.java:261) ~[AbstractMessageParser.class:1.7.10-1420.120]
at org.apache.http.impl.DefaultBHttpClientConnection.receiveResponseHeader(DefaultBHttpClientConnection.java:165) ~[DefaultBHttpClientConnection.class:1.7.10-1420.120]
at org.apache.http.impl.conn.CPoolProxy.receiveResponseHeader(CPoolProxy.java:167) ~[CPoolProxy.class:1.7.10-1420.120]
at org.apache.http.protocol.HttpRequestExecutor.doReceiveResponse(HttpRequestExecutor.java:272) ~[HttpRequestExecutor.class:1.7.10-1420.120]
at org.apache.http.protocol.HttpRequestExecutor.execute(HttpRequestExecutor.java:124) ~[HttpRequestExecutor.class:1.7.10-1420.120]
at org.apache.http.impl.execchain.MainClientExec.execute(MainClientExec.java:271) ~[MainClientExec.class:1.7.10-1420.120]
at org.apache.http.impl.execchain.ProtocolExec.execute(ProtocolExec.java:184) ~[ProtocolExec.class:1.7.10-1420.120]
at org.apache.http.impl.execchain.RetryExec.execute(RetryExec.java:88) ~[RetryExec.class:1.7.10-1420.120]
at org.apache.http.impl.execchain.RedirectExec.execute(RedirectExec.java:110) ~[RedirectExec.class:1.7.10-1420.120]
at org.apache.http.impl.client.InternalHttpClient.doExecute(InternalHttpClient.java:184) ~[InternalHttpClient.class:1.7.10-1420.120]
at org.apache.http.impl.client.CloseableHttpClient.execute(CloseableHttpClient.java:82) ~[CloseableHttpClient.class:1.7.10-1420.120]
at org.apache.http.impl.client.CloseableHttpClient.execute(CloseableHttpClient.java:107) ~[CloseableHttpClient.class:1.7.10-1420.120]
at kcauldron.updater.KVersionRetriever.check(KVersionRetriever.java:82) ~[KVersionRetriever.class:1.7.10-1420.120]
... 2 more
[17:39:28] [Server thread/INFO]: CONSOLE: Stopping the server.."
So now we can isloate the problem of being from KCauldron, you will probably want to try using different versions within your Minecraft version until your server is running. Another suggestion is to dump that and just try to use mods for your permissions need and etc (as the server only have to worry about mods not mods+bukkit which will most likely increase stability and decrease issues).