I'm hoping someone who uses the Kepler software can help with this.  I know how to do a bi-wheel and cast a current transit chart.  I can definitely see what planets are transiting in what houses, etc.  However, I'd like to know specific dates of when planets enter and exit those houses.  While Kepler can generate good, date-specific reports on planet-to-planet transits, I can't find ANY similar reports to planet-house transits.  I've searched the help file, the internet - everything I can think of.  Can anyone help?!?

Well, I've never used any programs to help me with studying my transits (although I'd love to if I had access to any). But, if worst comes to worst, you can try my method.
Pull up your birth chart on any easy to read chart like this: http://astro-software.com/cgi-bin/astro/natal
Now, you can also use this site to find out the chart of yesterday, today, tomorrow, next Thursday... (ie: the transits). What I do, if I want to know when a certain planet will be at a certain degree or different sign, I actually use a trial-and-error method. When you're familiar with the transit speed of each planet (and you can figure that out by seeing how many degrees each planet moves throughout the course of a month) you can estimate about how long you think it might be before the planet is at the degree of your house cusp, and simply type in a date that far in the future & see where the planet is. Taking into account that the planets go retrograde and such, it isn't something you can figure out with one try, but like I say, using trial-and-error, it really works.
And if you want to know the current transits (without using a program) I use this site: http://www.myastrology.net/ast-bin/current_planets.cgi

You need to learn how to use an ephemeris either book or online
http://www.khaldea.com/kldaephem/2000/apr2010gmt.shtml

Transits
I use--- 1' approaching, 1' exact and 1' departing. If you click on the link listed below for the online ephemeris it will list all planets at any given time. Learning astrology is like learning a new ‘language’ and obviously the more effort you put into something the more your knowledge and understanding will increase. All transits act as ‘background’ influences through a house, until it makes a mathematical aspect to a planet inside or an Angle.

For 'timings' I would look to the retrograde hit as the most important trigger, then look to see what the quicker planets are doing especially mars & mercury --

astro.com has fee six month transit forecast plus when you get into Extended chart selection, look at the three tabs after calculating a chart under ‘method’ default is circular wheels (on left), middle is special charts and in their you get graphic ephemeris 1yr (or 5years) with natal = transits for 1yr and lots more. BUT you first must learn or memorise the 'glyphs' ie: shorthand for recognising what these maps/graphics mean.

For example when you post or reply to a chart the 'smilies' to the right and just under them [more] if you click on there it will bring up a whole loads of 'glyphs'  Mercury  Uranus  conjunction (+or - 8')  trine aspect 120'  Libra
http://cafeastrology.com/transits.html
http://cafeastrology.com/transits_2.html
http://www.bobmarksastrologer.com/transits18.0.htm
http://www.astro.com/faq/fq_fh_transits_e.htm
http://www.astro.com/astrology/in_transits_e.htm
http://www.astro.com/swisseph/ae/2000/ae_2009.pdf
http://www.khaldea.com/kldaephem/2000/oct2009gmt.shtml
http://www.astrologyweekly.com/learn-astrology/astrology-glyphs.php
http://www.dkfoundation.co.uk/dkfoundation/BookTransitsAndProgressions.htm

Now it's more important to focus on transits from Jupiter to Pluto (poss mars as this is the ignition key)and these planets when aspecting something in your natal chart 'set off' the difficult or nice 'aspects - potential - problems' that your chart expresses. By that I mean if a benefic planet like Jupiter hits/touches/transits your venus, mars or uranus these could be experienced very pleasantly. BUT if your natal venus is afflicted, or badly aspected say conj saturn then jupiter will not has such a good effect. It all depends on how the natal planet is 'aspected'  

For me I would say external 'events' must be seen by transits, progressions or Solar arcs to Angles ie: Asc/Desc & MC/IC most other times these events are 'internal, psychological matters as in between the ears'