First off, PrimoPyro, you have got to get yourself the 2001 edition of Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (Fifth Edition) by Jerry March. This sucker is like Beilstein in one volume. I am not kidding. I only have the fourth edition (1992) but it too is fantastic! Bees are always saying that I have a knack for finding obscure references (right under Foxy2) but I'll let you in on a little secret: Practically all of my sources are actually from one source--namely the aforementioned textbook!
Anyway, to answer some of your questions (some from this thread and some from that other one of yours):
1.) Benzyl iodide could be had from benzyl alcohol by way of NaI or KI and phosphoric acid or by AlI3 (formed in situ through reaction of Al and I2). Al is otc; I2 can be had through reaction of NaI or KI and oxone). But toluene and calcium hypochlorite are more OTC, I guess.
Regarding pool chemicals, what about that "brominating" shit that they carry. I imagine that if it brominates, then it could possibly be used for brominating toluene or something.
2.) The amino alcohol that you desire could be had by reacting any epoxide with hexamine and then hydrolyzing the intermediate complex. Yields from styrene oxide and hexamine are, according to a reference that I've posted before, 100% of the desired amino alcohol (and by desired I mean that both the hydroxyl and amino groups are in the right place). To get the halohydrin, one could react the epoxide with AlI3 made in situ. Iodides are easier to swap with amines so this might be preferred over reacting the epoxide with HBr (which isn't all that OTC, BTW) and going from there.
3.) As for your question about whether or not aryl chlorides or bromides could switch for aryl iodides in the Ullman reaction, I refer you to "3-16 The Ullman Reaction (De-halogen-coupling)" on p 665 of the aforementioned fourth edition textbook:
". . . The best leaving group is iodo, and the reaction is most often done on aryl iodides, but bromides, chlorides, and even thiocyanates have been used."
Hope this has been helpful. However, the best advice that I have given you is to buy that fucking book. Enough said.