If you find someone to pay more and break your contract you will just get sued and lose out anyways.

Family and business usually don't mix well and when it comes to family losing money, then it really doesn't do well. 

If that happens early on the person contributing the money loses and the person contributing the work wins out financially.

So you may net a few bucks every month in reality, but on paper you are losing money once you account for the whole picture.

He is an excellent tenant and I don’t want to lose him but understand that people move on.

I've seen more wholesalers lose deals, simply because they didn't have a buyer. 

It might be a good time to evaluate 2 things. 1) What are the risks of your company going bankrupt (at which point your 401k disappears); or the stock market losing your money in a recession, depression or government default before you are 59 1/2, as opposed to taking a 10% penalty and having the money free and clear?

Otherwise, I'd say it makes sense to manage your own properties until it becomes such a task that you begin losing money due to opportunity cost.

I’ve spend years with wrong subs and losing money and over paying etc to get the crews that I have and even still today I replace guys at times.

@Kevin GlassbergA syndication is just a cool term where a sponsor / general partner / deal finder pools money from limited partners / those with money to purchase an asset that will provide cash flow and/or appreciation.Syndications can be in start-up companies, venture capital funds, stocks, bonds, or real estate.We are on a real estate forum so we can discuss real estate syndications.A real estate syndications big sell is that it is hands off for the investor who doesn't have time to manage along with access to deals that he/she may not be able to do on her own.The cons are that you lose some control along with having a hold period that is normally dictated by an operating agreement(illiquid asset).Best of luck