I've had similar issues with my TopGuest account ... I use the m.foursquare.com method to check-in (even though I am usually within 0.1 miles of a BW/HI Express/Doubletree some point during the day, so GPS should work). I've done 7 check-ins on foursquare in the past few days, but only 4 hit TopGuest. All have been "off-the-grid," but they've worked in the past so that shouldn't be an issue.
I checked in at a Doubletree at 3:59pm pacific, and it showed as same-day. However, the Best Western at 7:55pm pacific showed up as next day. So I agree that there's a late afternoon cutoff somewhere. Kind of annoying, but I'm not going to look a gift horse in the mouth.
(Actually, I just saw that I checked in at the Doubletree at 7:30pm, then 3:59pm the next day, but they counted as the same day, so that's why it didn't count twice.)
Also, if you're worried about keywords, search for valid locations
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Lastly, I don't think using 4sq + facebook will work, since you're looking at a maximum per hotel chain within the TopGuest program per day. Different TopGuest accounts can work, but I don't want to be a target for a shutdown because of 50 pts/day, so I'm going to keep my 1. This program serves a great function ... a family member is 400 HHonors points away from 10K, which is what I'll need for a GS hit if that program returns. This is such a simple way of topping off.