Different lenders, different decisions. With one lender, the hot tub and pool table on the contract wasn't a big deal or red flag. With another the childs playset was. What is the difference between the two?

The underwriter is the difference.

The hot tub may be considered "attached" at which point it becomes part of the real property being sold. The childs playset could also be considered "attached" if it is not just resting on the ground (I remember my old one was cemented into place in my back yard). Anything else can absolutely be referenced in the contract as a contingency (the sale of this house is contingent on the successful sale of the pool table from the seller to the buyer), but should be sold on a separate bill of sale and paid from separate funds. The bank doesn't want to finance your pool table - they want to finance your house.

Ultimately the decision is up to the underwriter who handles the loan in each particular scenario, so there's really no way to definitively predict what will or will not be allowed.

We sell a lot of personal property and always use a separate Bill of Sale (typically for $1) that is referenced in the contract. Lenders don't question it and the property sells at the same time as the house.

We don't reference it on the contract at all, and just have it as a separate bill of sale.

I believe a seperate bill of sale outside of escrow is the best way to go on this. It shouldn't even be mentioned in the contract if it is something personal. Like someone said above, the lender does not want to loan money on a home plus personal property because it could change the value. They just want to loan money on the home by itself.

Most of the homes I sell are second homes and all have some form of personal property included...some are completely furnished and have boat docks and lifts. Prior to January or so of this year the "local" banks didn't have much of a problem conveying these personal items with the sale and appraisals included the boat dock in the value. Fannie and Freddie changed their guidelines early this year and docks were no longer included in the value and the appraisal reflected this. This can cause lots of problems when you have a $40,000.00 dock included in the sale and the appraiser does the typical "drive by" appraisal and just deducts 40k off of the selling price...buyer has to come up with an additional 40k at closing or take out a personal note on the dock at a higher interest rate.
In my area underwriting and the appraisal is the key...if it is a local lender the process is usually smooth but if it is an out of state lender and underwriting is on the west coast (no offense here) be prepared for a long painful ordeal.

I always insert the verbiage "personal property has no monetary value and is being conveyed as a convenience to the seller" in the contract.

Personal property conveying is kind of a Catch-22 deal...if you reference it in the contract it can cause problems and if you don't reference it in the contract and it is included it can cause problems.

I have never heard of this being an issue but does bring up a good point. I will keep that in mind now.

We sale the personal property with separate addendum.

We reference the bill of sale in the contract so if the house doesn't close the buyer can't come looking for the furniture and if the furniture is not there at closing then the buyer doesn't have to close. We sell a lot of fully furnished houses.

Never had a problem with it in 20 years.