I've shared this page of Jake's site before, but I'll post it again here as I feel it's relevant.
http://www.flat6innovations.com/engines/performance-parts-a-services/5-performance-engine-modifications
Have a look through there and see some of the other options you may have overlooked.
You have a 2.7 that's putting out somewhere around 220hp crank (on paper), right? Here, aside from doing intake, headers, exhaust, and tune to start, Jake can take your block (if it is worthy

), remove the lokasil cylinder liners and have nickasil ones installed (Stage 2 on the web page). The advantage to this is that you can actually bump your 2.7 up to a 2.9 if you want with the installation of the nickies, and the job comes with new pistons, rings, and pins, and you can get stronger connecting rods for a small bit more. He can also do light machining on the heads to improve their performance with the new displacement. Even if you left it at a 2.7 it would bring a slight performance increase just having the nickies in there. I'm sure that if you haven't done the IMS retrofit or upgrade yet that it can be done during this process, as well.
And this isn't even getting into the next stage of turbocharging, if you so choose. If they can pull 300hp from a 2.5 with just what's on that page, at what appears to be maaaybe approaching the same amount as the cheapest price speculated in an earlier post, I'd say consider some of these options. I have to imagine if you're starting out near 220 stock that you'd have to be approaching a few tens of hp shy of 300 crank with a tuned 2.9 with modified intake, headers, exhaust, and tuning by Jake (normally aspirated still). I know that's not the 300 wheel you're looking for, but a good deal of that (and a nice heaping full of torque) will be hitting the ground better than before, and you'll still have a more reliable engine the way it should have been built.
Now, I've seen no hard numbers for it, it's just my speculations. But it's a question you can ask Jake, and I doubt he's going to have a problem with you asking him questions about something you're considering having done through his shop. I would imagine he expects more questions than he gets. Anyways, I just wanted to put that option out there in case you hadn't come across it yourself when looking around his site, because to me it means no need for a whole new engine, because you'd pretty much be getting one out of your original block when Jake's done with it, and you'll still be getting a serious bump in performance without needing to really get rid of your original engine.
As far as the other bits go, if you're looking to add nearly 100hp to the equation, you're going to need to stop better, as you're undoubtedly going to put that power to the test. If it were me, I'd want to be able to stop just as well as I go. You really might be fine just getting better pads, you don't necessarily have to go and get big cross drilled brakes, but that's not really the discussion we're having so I won't go down that path here.
Hope the link above is helpful in some way, and do try to get in touch with Jake, I'm sure he'll be quite willing to answer your questions.