One part I am looking at is flipping one house a year, netting $14,000 in broker commissions and about $18,000 in profits after all expenses, for retirement.  

Regarding how to structure my business - I do not have an LLC setup as an agent and just plan on purchasing properties under my investments LLC, then getting paid as myself for my commissions.

If you'd be in default where seller can sue you for damages above earnest money and real estate agents can sue for commissions, then you may want to consider those potential costs before making your final decision. 

Them kids don't get any buyer agent commissions anymore so they're all Uber drivers now.

the answer i'm giving is based on the assumption that you do not want to / can not float the negative cashflow any longer. and note: even if appreciation / debt paydown / tax benefits strongly outweighed the negative cashflow, most investors wouldn't want to / couldn't float that. so that said, i say SELL. you have just over a million dollars in equity (minus transactional costs when you sell), and you could do a 1031 exchange into a ~4 million dollar CASHFLOWING property. i invest long distance into value-add multifamily on the west side of chicago. gearing up for my next deal right now. in that price range you could easily get a value-add multifamily with potential to cashflow 15k/mo+++ (up to 40k/mo) once it reaches its full potential. it sounds like you're in markets that are probably strong for appreciation and weak for cashflow (with the long term rental strategy). if cashflow is your goal, 1031 into value-add multifamily in a higher-cashflow area. don't let having to pay commissions during the sale stop you. you're already losing so much annually; you have to stop the bleeding at some point. also note that right now, with the way these two properties are losing money, that might negatively affect your borrowing power when you go to buy the family home. feel free to dm me if i can help in any way!

The National Association of Realtors know as NAR 'settled' the class action lawsuits over conspired commissions and essentially surrendered with far reaching impacts on the industry and real estate investors.

Regarding how to structure my business - I do not have an LLC setup as an agent and just plan on purchasing properties under my investments LLC, then getting paid as myself for my commissions.

File a complaint against him with the Real Estate Commission for not returning the funds to you nor filing and interpleader relating to the funds.

Under commissions or Other?

@Amirra Besh If you call any agent, they will typically charge 1 month of rent to find a tenant.Just like in a sales transaction, where the buyer's agent and listing agent split the commission, an agent will offer another agent that brings a tenant 50% of the one-month of rent as commission.Many owners are trying to put pressure on PMCs to lower this fee because they think the monthly management fee should cover at least part, if not all, of this.Here's were penny-pinching owners screw themselves: PMC's will charge lower than the one-month of rent, but they offset it and do NOT tell the owner the negative repercussions!