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Hi, Matt. As for retirement plans (can't help you with the cafeteria/health stuff), ASPPA is good for education and credentials. I don't know of any trade show specifically for software. The main players for small TPAs are FTWilliam, Datair and Relius. I'll point out what anyone else who posts here will likely point out - trying to "get in" to the pension administration business from a point of zero pension administration experience is ill-advised. You'd be better off hiring someone or better yet just forming a relationship with a consultant who can provide you the expertise in a way that you can pass through as a value-added service. If you do that (the latter) for a while and decide you want to push into that business, you can maybe then do it from a position of strength with a bit of support from someone already in the business.

I am from the health side, so I cannot comment on retirement issues. Agree with comments made about hiring someone with experience if you do not already have someone. As a former CEBS instructor, I can tell you that "book learning" is only part of the equation. There is only so much that educational programs can provide. Over the years I have found that sites such as DOL, IRS, Law Firms, SHRM, etc. have provided better information because they tend to describe issues in terms of implementation and often times discuss the pitfalls to avoid.

I don't think this is accurate for a Roth account. Interest payments are made after tax, of course, but the earnings on a Roth account wouldn't be taxed when distributed.

With respect to your Point "4" above: "Past performance is not a guarantee of future performance." Retirement plan investing is LONG TERM, and the past 2 years are but a blip in the time horizon. Plus, when the market is low, you are "dollar cost averaging" into cheaper shares/units which, when the market rebounds will magnify the upside.

some of this stuff you really have to hunt down.... 1.410(b)-5(d)(3)(ii) .....on the basis of plan years ending with or within the same calendar year (but you knew that and was checking to see if I remembered, which I didn't but had to look up again)