You are in a difficult situation down in FL, with a softening marketplace, with current and future comparable houses for sale.
Jim Howard presents both sides of your situation very well. . .
The question is how long do you want to wait to sell the house?
If you want to sell the house quickly, then updating everything and selling it as the lowest priced house against the comparables is the way to go. . . the house will appeal to more buyers. Otherwise, you are waiting to find more of a flipper buyer and he/she will want to low ball you on the price as his profit will depend on how low of a price you will go. ie you are appealing to many fewer less buyers, and will probably wait longer for that higher priced flipper, more price sensitive buyer.
In prepping our current new england 20 year old house for sale, we are doing all the "modernization" spending prior to sale, knowing that it won't increase the price against the comparables for sale, but it will attract more buyers who want a fully functional house being move in ready for worry free living, therefore a quicker sale. Just signed a contract for a new roof, 50 year warranty shingles, for $9,000, kitchen appliance upgrade is done at $5K. However oil furnaces are now prohibited for new builds, so a new oil furnace replacement is $25,000 plus . . . only electrical heating is now allowed. . we haven't decided on what to do with the oil heating system which is still functional.
we feel your pain. . i would go with the upgrade for a larger pool of available buyers who are willing to move in as a retired couple looking for worry free house. . and not attract flippers who will low ball you for more profit for them. .
good luck
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