Leaderboard

Owner1 would own 60% and the wife would own 60%. But you don't add them for CG purposes (no double counting). You use either one of them. My approach was to consolidate ownership percentage for one spouse, and completely disregard another spouse for CG determination purposes. In this case you will have Company A Company B Owner 1 100% 66.67% Owner 3 0% 33.33%

You are working way to hard, and just asking for trouble. Pick a safe amount close to the 415 limit and use the maximum funding limit to keep the plan overfunded. Then, in the 9th year, or when he starts wanting to terminate, calculate the maximum benefit and make sure the assets don't exceed that amount. This works great, especially if you don't have any other participants. IMHO, the 415 limit is too fluid to try to match every year.

Wouldn't it be better to do a Roth inplan conversion immediately?