Don't ever get pushed into a deal. You have to control all elements at all times which admittedly can be difficult at times.
Nothing I say should be substituted for legal advice from your attorney.
One of the hardest things in this game is finding a happy medium of trying to help and make the seller feel comfortable but also sticking to your guns on certain things.
Absolutely under no circumstance would I write a check to a seller. I am sure that you know this. The hidden motivation here is that this seller most likely is wanting some cash now. "Mrs. Seller I will provide the EM to the title company and they will hold it until closing. I am not going to pay someone cash outside of a closing because a clean title can't be proven and that would be a horrible business practice on my end." Write the check and tell the Title Company to hold the check and do not do anything with it until closing. I have 2 title companies here that are happy to do that for me. If they give you issue regarding it, then I would really just flat out say " Mrs. Seller, that just doesn't make any sense to me nor do i know any other investor that would take such a risk. If we don't get this done and started now, what else are you going to do with the house and the squatter that is now living in the house?"
In regards to #2 - "Mrs. Seller, you are trying to sell a house at the end of the year and a week away from holidays. The title companies are getting swamped with closings from banks and other institutions for the end of the year. The will need to check on the title for liens, or judgments against the house or you and any back taxes. They will need process all the necessary paperwork, send it all to you and get it signed in front of a notary, and then have it sent back.I am simply at the mercy of the title company and the longer we wait to get it started the longer it will take as the end of the year approaches. If we don't get this started right now and get it done, what else are you going to do?"
I also would probe a little bit. If they were asking about the Earnest Money because they need the cash now then I would push things a little different. I might say "Mrs Seller... I have never been asked to pay EM directly to a seller... I can't help buy be curious... are you needing the cash or something for Christmas?" If they said yes I would totally restructure the deal. "well let me call my guy down at title and see what he can do. If I can get you the $1,500 as quickly as I can which should be 7-10 days could you give me 4-6 months to pay off the rest?" I have negotiated deals like this successfully and given myself a 0% interest loan on the house to rehab and sell it because the seller needed a little cash now. Obviously use your best judgement as to if that is worth pursuing.
We Buy Houses. We don't have them sold to us. Tell her that is how you do business and if it doesn't work then move on... but follow up a week later ;)