I'm surprised how anathema bottling is to some people. I actually kind of enjoy the process, and I really like being able to both easily share bottles with friends/family. Also, it seems like kegging doesn't remove the hassle of bottling, it is just a different process. I sanatize bottles in the dishwasher, which is easier to me than sanatizing a keg, and I mess with priming sugar instead of a CO2 tank. I need a dark room temp location to age beer a couple weeks, instead of a repurposed refrigerator/freezer and temp controls. I grab beers from the fridge and uncap instead of installing a single-purpose kegerator.
In fact, I came across a free fridge recently which I was originally planning to turn into a kegerator...but the more I think about it I think it will just be summertime fermentation chamber for the time being.
In the perfect setup with a lot of extra cash I would totally keg and then bottle a few for sharing...but it seems like more of a different process to me as opposed to an upgrade of the process.
So long story short, I would vote going AG (which i know you already decided on...but in case anyone else has a similar internal debate). Using the BIAB method, there are very minimal costs associated with AG, and each batch of beer will cost less (grain is cheaper than extract) so you can save money faster for the eventual keg upgrade if you want. With kegging you might save on bottlecaps and priming sugar, but it will be offset by CO2 fills.