Ultimately I would like to move into consistently flipping homes and even owning some residential rental properties so that I have a solid monthly income based on however rental properties I own in the future.

Steve, I'm sorry man but while I get what you are saying ultimately your saying you have people that can't do their frigging job of paying some attention to detail and doing math. 

BP is the ultimate real estate investing site around!

My ultimate goal is to achieve financial freedom so that I can spend more time with my loved ones, travel more often, and help those in need.

(Ultimate Goal)Goals will change and adjust based on circumstance and perhaps it's wishful thinking, but I'd like to start with the end goal -both short and long term- already in mind and formulate the plan to get there.

There are so many factors that play into keep vs sell decisions, but ultimately your strategy should be based on your end game.

I'm hesitant to let go of that, but selling would free up a decent amount of equity (in our market, I know 25k isn't much in most areas) to make a decent down payment on another multi-family, which is what we ultimately want to do with our REI careers.  

He clearly has trust that I can perform, we’ve done over $1.5m in deals together, he just ultimately doesn’t want the properties and loan “in his name” when all the dust settles.

Again, this is only a recommendation, which I would do if I were you—however, that is ultimately decision".

Thanks for the shout @Chris Bodden@Kobi Pesi As you are looking into the Cleveland area the 1st thing you should do is read The Ultimate Guide to Grading Cleveland Neighborhoods to familiarize yourself with the market.