To all the * Award experts here:

Is there a limit for connections for an award ticket?
I am trying to go from SFO to HKT(Phuket). I called UA several times and they said the only routing available for the date I want is on SQ flight from SFO to ICN, then TG flight from ICN to BKK, then BKK to HKT.
so, SFO-ICN-BKK-HKT, we are talking about 2 connections.
However, this routing requires 8 hours layover each in ICN and BKK.

I then called back and asked for availability from SFO to BKK, and I got:
SQ1 from SFO to HKG, then to SIN, then SQ64 from SIN to BKK
then I called again and asked for availability from BKK to HKT, and I got:
TG221 from BKK to HKT

Now my quesiton is why didn't the first agent tell me that the routing is available from SFO-HKG-SIN-BKK-HKT (3 connections, but layover is less than 2 hours at each connection). The previous option has 2 connections (ICN, BKK). Is it because there a limit to the number of connections?

I now have two reservation SFO-HKG-SIN-BKK, and BKK-HKT. Can I ask UA to combine them? this way I can save 20K miles.

I appreciate your input.