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Each antenna by itself worked great.
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So, go back to what worked... If it still works well, let's build from that. If not, determine if the antenna is in trouble, or the coax, or connectors, etc. (Rubber boots make great funnels to pour water into the coax. And compression connectors are vastly superior to crimp type.) Have you done this test?
http://forum.tvfool.com/showthread.php?t=13646
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Well, that worked for a while but the issue was the combiner could not seem to figure out which signal to push...
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A broadband splitter/combiner is quite unlikely to work in this application. At a minimum, passive filter type combiners need to be considered. Tinlee.com AC-7 for example.
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Are there any long range VHF only’s out there?
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If you prove the Winegard(s) bad, then yes, the Antennacraft Y10713 is the top consumer grade H-VHF option. (The 91XG + Y10713 make the top of the list for consumer grade deep-fringe/DXing off the shelf options.)
Once you have a west antenna working, and an east antenna producing reliable reception, then we can talk about amplifiers and combiners. (You may also want to consider a few alternative options such as a PVR/DVR that can be moved or one that has detachable media (hard-drive).