I figured I'd share some of the steps I took to make things simpler and run on autopilot. It's a abbreviated and shorthand list, but hopefully it helps people think about what is possible. Most of the steps listed are consolidating accounts as much as possible while still attached to specific employers, and also putting things on autopilot. It took several months to get all this done, but it's well worth the effort.
1 move T's Scottrade assets to Vanguard
2 move T's TIAA assets to Fidelity
3 move DW Scottrade assets to Vanguard
4 Request U TDA Vanguard plan #
5 Determine TDA and DCP funding levels
6 Fill out U salary reduction agreement to max out the TDA @$17,500
7 Open Vanguard TDA account
8 Determine best F DCP vendor
9 Ask ICMARC about all fees
10 Open F DCP with best vendor
11 Fill out F salaray reduction agreement to max out DCP to $4000 for 2014
12 Fill out U HSA change form to max out HSA
13 simplify asset allocation with a few index funds
14 invest HSA money into VFINX, 500 index
15 rollover SBS plans to Vanguard accounts to avoid higher fees
16 transfer DW WI teacher retirement account to Vanguard
17 Obtain both original Disney stock certificates
18 biweekly mortgage payments, start in Jan 2014 at a second payment of $500 on the 15th, if cashflow warrants
19 set up automatic Roth IRA deposits in Jan 2014
20 set up after tax account at Vanguard
21 set up automatic after tax account deposits
22 prosper vs lending tree?
23 where to invest extra $ after car paid off ($1500/mo, $18k annually)
24 where to invest salary increases?
25 automatic investment into T's money market account of $1000/month ($500 2x/month)
26 once above reaches $3000, invest in VTSMX from MM or bank account and set up automatic investment from bank acct
27 Increase DW 457/DCP to max at $9000 for 2014
28 Increase DW 457/DCP to max at $17,500 for 2015