All it is is a job where you are compensated for bringing a buyer and seller together...To do it properly took me about 10 years of being in the trenches of buying, selling, landlording, and doing a few bad flips.

While underwriting considerations given to compensating factors may carry the day for you, I find raw numbers have their own value as well.

If both parties are unrepresented, and you just make the connection and want to charge either or both of them some kind of consulting/admin fee, that would conceivably be allowed...if your broker allows it*, and the if fee is paid to your broker.The customer always pays the broker, and the broker always compensates the agent - you can not be paid directly by the customer as a sales associate.

On a serious note, actually it doesn't really matter if the cleaning person is a family member or not, I think that any person who provides a professional cleaning service should be compensated for it.

Of course you'd have to compensate your partner, and adjust your numbers accordingly.

I would ask the HOA for compensation but I doubt they will do this.

Take a bit of the rent to compensate her for the monetary outlay, if the window unit cost 200 then reduce rent by 20 per month for 2 years ect.

There's also the matter of compensation.

I'm neither a lawyer nor an accountant, but I recommend Googling "closely held corporation" and then asking your tax accountant how, if any, the proposed idea might impact your overall tax situation (https://www.irs.gov/faqs/small-business-self-employed-other-business/entities/entities-5: A closely held corporation is subject to additional limitations in the tax treatment of items such as passive activity losses, at-risk rules, and compensation paid to corporate officers.).I've read that when two closely held corporations owned by the same small group of shareholders do business with each other, the IRS sees a red flag because some people try using this approach to evade taxes.From my readings of personal finance articles, this additional scrutiny is based on whether there is an "arms length" between the two parties in a transaction. 

do you have registered securities folks selling your investment memberships.. somewhere I think i learned that only registered series 7 type folks could get compensated .. if they were NOT employees of the mother ship..