Will have to do some reading to learn how to interpret what I'm seeing on APRS.FI, but interesting to note that while the igate near me was able to hear my packets when I drove near it's QTH. But when I held my HT up while standing in the back yard, that same station which was a couple miles away didn't receive my packet but a digipeater about 16 miles away did.
Good job!
Were you adjusting your packet path? From the raw packets shown on APRS.FI, it looks like there were some different paths in use...
2018-06-17 01:20:15 UTC: K5GTI-7>S2SW0W,qAR,KD5DK:`}^ynp,[/>^
2018-06-17 01:21:16 UTC: K5GTI-7>S2SW1R,WIDE1-1,qAR,KD5DK:`}^flpW[/>^
2018-06-17 01:23:17 UTC: K5GTI-7>S2SW1R,WIDE1-1,WIDE2-1,qAR,KD5DK:`}^el!v[/>Figuring out APRS^
2018-06-17 01:25:18 UTC: K5GTI-7>S2SW1R,WIDE1-1,WIDE2-1,qAR,KD5DK:`}^el!vY\>^
2018-06-17 01:29:20 UTC: K5GTI-7>S2SW0Y,WIDE1-1,WIDE2-1,qAR,KD5DK:`}^xl"qY\>^
2018-06-17 01:30:20 UTC: K5GTI-7>S2SV7T,WIDE1-1,WIDE2-1,qAR,KD5DK:`}_"o+vY\>^
2018-06-17 01:31:21 UTC: K5GTI-7>S2SV2Y,qAR,KD5DK:`}^ro5PY\>Figuring out APRS^
2018-06-17 01:41:48 UTC: K5GTI-7>S2SU9W,K5FTW-5*,WIDE2-1,qAR,K5UTD:`}]3l (Y\>Figuring out APRS^
The first and seventh lines above appear to show the number of digipeaters selected in your radio was zero, and the second line above shows only one hop was selected. Lines 3 through 6 show KD5DK directly heard you, when you had WIDE1-1,WIDE2-1 as the packet path, and the last line shows that your packet was digipeated by K5FTW-5 and then picked up by K5UTD where it went into the Internet.
As for why a nearby digipeater won't hear you, but a digipeater farther way will hear you... hard to say. It's possible the antenna on the nearby digipeater is directional and not favoring your location, or that digipeater was hearing another signal (or interference) at the moment your radio was transmitting, or maybe some other interference popped up at that moment. Something could have interefered with you while you were transmitting, preventing the digipeater from hearing a complete packet from you.
73!