Second, I remind the tenant that if flooring is replaced and they happen to damage it, it will be costly and come out of the security deposit whereas if they damage already very old carpet, they will not be charged for replacement, no matter how badly they may have stained, torn, etc. the carpets upon move-out. 

I would have given the deal to the listing broker, but Vt is not a dual agency state and at the time, I was a Californian so I needed a broker to look at the property, handle paperwork and give me guidance as I was unfamiliar with Vt real estate practices.I've bought several properties that took 5-9 months to make deals with stubborn sellers Government agencies or banks in order to get them to accept my offers.

@Andrew Johnson  Thanks, the windows and trim are all stained wood and not painted but the soffits could be an issue. 

The cheapest option (other than nothing) would be to make a cut in the middle and remove the old, then acid stain the driveway so it all matches. 

I fully understand there is normal wear and tear on carpet (this carpet has been used for more than 6 years), but due to the strong smells of cats and carpet stain, we have no choice but to replace it.  

Don't you just hate it when you've waited years to get back in the game, and the market still stubbornly rises?

I've sold flips with old water leak signs, however it was simply because I didn't clean or paint the stained area and the leak wasn't active.2.)

Try to keep emotion out of it and be prepared to walk away if they are stubborn.  

Some sellers are just stubborn and you have to let the market season them a bit.

Bless all careful inspectors.Improperly installed bathroom vent leading to active, long term leak (huge black stain under the roof, small stain on bathroom ceiling)Broken (!)