Drilling a hole in a joist

I live in a split level duplex, and one part of the lower level used to be a garage that was converted to a living space. The house is on a somewhat level part of the parcel with the back 1/2 of the back yard uphill, and the front yard almost all downhill. Therefore, the garage floor is a little above grade towards the back yard and is at grade towards the front where it meets the driveway. I suspect the yard isn't graded properly because when it rains heavily there is standing water next to the back part of the house and part of the garage side. However, despite the standing water at the back, the two places water comes in after very heavy rains is by the side door to the backyard and where the driveway meets the front wall. I get about a 3 ft. wide puddle by the back door and about a 1 foot puddle 3/4 of the length of the driveway wall. Neither puddle is deep; they're just a nuisance and keep everything damp and keep me from finishing the floor. I had B-Dry Waterproofing come in last year and they said they mostly did sump pump type work and that my problem wasn't serious enough to warrant that kind of solution. So I don't know exactly what to do next. My inclination is to wait until things dry out (if that ever happens here on the East Coast!) and caulk and apply waterproofing "something" the outside area where the driveway meets the house and also apply waterproofing to the outside of the foundation on the side of the house (after digging down about 8 inches). Although it probably would be a good idea to install some kind of outside drain to pull the water away from the back and side of the house, there is a deck the full length of the back plus a wrap around walkway to the side garage door, which restricts access. Would there be any benefit to trying to put in some kind of drain running from the back of the house (from where the deck stops) around the side and to the driveway where it can run downhill? And I guess the last question is whether I can do any of this myself or if I should get a professional. I'm a little handy, but this stuff is all new to me. Thanks to all, Beth

How do you connect or leave the VB at ht e top of a conc. block basement wall? I have an older home (50's) with no gasket along the top of the wall, and the joists sit right on the block. Also, should the VB on the conc. slab under the sub-floor be continous with the one on the wall? Thanks in advance.