It's a little hard to respond without knowing what #2 is.
FWIW...Keep in mind I'm not the sharpest tack in the box -
I'd suggest that you think about either a 7 or 9 (fly in each - have your wife fly in each, and pick the one you like - very difficult to make a mistake). Personally, I lean toward the 7 (for you taildragger sounds right).
As to #2, buy one now to keep your flying skills up while you're building and accomplish the training you mentioned. Just buy it right - so you can sell it right.
I've got nothing against the toolbox - but I would recommend that you go right to the tail kit (and get a little help to get off to a good start).
Relative to qualifying for A&P - the requirements that you should focus on are part of 8900.1 (see
http://fsims.faa.gov/PICDetail.aspx?...Vol.5,Ch5,Sec2 ). However, it's not at all unusual to hear of other anecdotal requirements thrown out by FSDO staff that present insurmountable barriers even in the face of the written guidance. You should get to know someone at the FSDO (who isn't going to retire or transfer any time soon) and an A&P/IA. Do your build and an engine overhaul. Have the IA function much as a tech counselor on the former and do the latter under supervision of the IA. Keep them aware of what you're doing and ask for advice. If you do buy a #2 to fly while you're building, you could do "owner-assisted" annuals and as much work as you can that can count toward your requirements. Keep a record of what you do. When you're done, you'll be much better able to get a letter of recommendation. (Better to have the camel in the tent p****ng out than the other way around. I also would recommend the Lycoming engine school - it was excellent.) It may take some determination.
Hope that helps.
Dan