I know he has done reissues of his first three LPs (Everything I Long For, The Closer I get, and Skyscraper National park), they were done really well but sold out quickly. I have OGs of them all (minus The Closer I get which never saw a vinyl release until the reissue "series"). I wouldn't be surprised if we get a reissue of Elk-Lake Serenade soon. I don't know though if the pervious 3 will be reissued again any time soon. Pretty sure he did all the reissues all himself, and he did not skimp out on the quality.
The lesson I've learned with Hayden, don't wait, he may not be a big deal in the USA but he has a cult following here, and obviously does pretty well in Canada. He is playing Massey Hall in May and it's super tempting to fly out for that show. it won't disappoint, especially the shows he's done recently just by looking at the set lists.
I think the only thing of his that has not come out on vinyl is the live record he did, which has a killer cover of Neil Young's "Tell Me Why" Also would not be surprised if that finally gets issued on vinyl (could be a good RSD title for Canadians)