The US automatically assumes every person coming in will attempt to live in the US and overstay their visa. This has been the practice for years. Nothing to do with Trump, although I don't imagine any easing of that mindset under him.
Sure. And there are literally hundreds of VOIP alternatives to Skype that can make those calls. A 30 second or less Google search will list the top choices with a breakdown of each. 10 seconds using AI search. Skype hasn't been the only game in town for a long time now. Posting on FB, waiting, and then sifting through dozens, if not hundreds of opinion replies is like searching for answers on dial-up BBS's.
At which land crossings? I'm planning on crossing the friendship bridge and to Vientiane, staying 7-12 days, then returning for another 60+30. It will be my first time exiting and returning after my initial 60+30. Never been to Thailand prior.
After that 90, I was planning to return to the US for 6-8 weeks, then probably do Vietnam, Cambodia, etc... for a few months before attempting to re-enter Thailand, probably on a different visa by then.