Unless they are asking for a commission amount that is out of the ordinary just pay it and get the lease signed before something changes.   

Brit, you do not have to wait 6 months, fyi. 

With a fund some can offer tax preferred treatment such as dividend vs ordinary income so it’s something to review not just gross but net returnsThere is no right or wrong answer to this, it’s truly a preference and how comfortable you are with each type of investment

For questions #3 and #4, you need to have a reasonable and ordinary expense for doing this, and you would likely need to track usage. 

What you're proposing is the conversion of ordinary income subject to SE taxes into deferred capital gain, OR potential exclusion of the income all-together under IRC Sec 121 if the property is to be your residence.I've seen no reasonable basis for such a position.

You thought an extra $240k, they thought an extra $300k, and you settled on $270k.The new taxation for the seller is:- nothing now- if exercised in 2025, they sold the property for $330k in 2025- if expired in 2025, they keep your $60k and report ordinary income of $60k in 2025

@Kevin S.When you take RMD from an IRA or 401k, you pay ordinary income tax on the distribution amount.

Since that decoupling, there has been a long stream of "rah-rah" shows that IMO did not focus on ordinary people, bringing a sense of reality back to the process, and inspiring people not by stoking BS dreams of Grant Cardone (who's Grant Cardone, my long-running joke) but by highlighting how your any wo/man could do it, in a realistic way.

Also check to see if the lender is going to issue you a 1099 C.. this will be ordinary income to you and tax will be due..

@Brit Hale - Thanks for reaching out to me, I can always count on the BP community!