Jeremiah,
Believe me, long timers are still facing this dilemna.
I am going to tell you how I have solved this problem. I fixed me a goal, the gokaden. Now, I was on a limited budget each time. So it was a question of waiting for the "Deal" in each school. I found opportunities through Darcy's website and thanks to him and his kindness, I found my Soshu tradition (Tametsugu) and my Mino tradition (Naoe Shizu). My Bizen sword (ubu Yasumitsu) was found in Japan. I saw it on display, alone. Early Kamakura sugata with Ko Kissaki, incredible fumbari. A friend negociated it for me, I got a 10% discount. How many ubu tachi from Yasumitsu in this style one can see? I don't know but I have never seen its like. My Yamato sword, it was very difficult, all that were available through the years had defaults, including the available Juyo ones. Then my friend Bob H at a DTI had a printed list of on consignement swords (not on display). Among them, there was a non papered Yamato one with two sayagaki, one by Honma Junji and on the ura by Tanobe sama. The blade was fantastic, no kizu, pristine and furthermore reasonably priced. I could not resist. I bought it (I got a reasonable discount from Bob) and put it to shinsa, came back as Tegai Kanekiyo, late Kamakura. For my Yamashiro blade (Ryokai), Bob was there and found it for me with a good discount Bob H is a lovely guy, so friendly. He can find almost everything you want at very competitive price. I almost never negotiate with him, I ask him what is the best price he can give me and it is always in my budget.
So the swords came to me on their right time but I had made up my mind from the start and did not jump on the first passing by. It took me years
Since Gokaden were completed, I bought two tanto. A yoroi doshi (1cm thick), I always wanted one and a Kamakura signed Yamato Senju'in tanto by Sukemitsu (http://www.militaria.co.za/nmb/topic/19201-kantei-for-fun/), this one was for me, late Kamakura Yamato tanto are very rare, but a signed one by a Jo saku smith, it is the Holy Graal.