Perhaps you could form an LLC later on down the line to clean up the structure after some time.That way you'll be able to do clean 1031's with your new partner from property 2 --> property 3 ect.....

The service company can attempt to extend its life by cleaning the condensing unit, replacing the aged AC capacitor and contact, and checking for R-22 levels.

Save the money, clean it till it shines, maybe basic improvements like a few new light fixtures or at least matching/bright lightbulbs, maybe a few new faucets, some paint touch ups and sell.If you’re hiring a Realtor®, they can tell you pricing in current condition versus pricing with a few minor changes.

I'm on the fence with a mid grade carpet that gets replaced with each tenant, versus a higher quality that can stand up to stains and cleans well. 

We have a pretty solid lease that has served us well on our properties but on the most recent move-out by a long-term tenant that always paid early, we had to clean from floor to ceiling and everything in between. 

Because of this, they have changed their fee structure on me two times in the past two years2) They don't have back up cleaners so when the cleaner can't clean, they block off my calendar3) They do not have easily legible financial statements and do not provide 1099s 4) They have made decisions that have required my money without consent5) They block off check-ins on Sundays6) They are not great with technology - though they try to use hostfully to list on many platforms, I will frequently see that my listing is not up on VRBO for example.

Steam cleaned the carpets, etc, and he determined there was no damage.

As a newbie here, my greatest challenge is consistent, reliable, high quality, detail-oriented cleaning.

I have properties in the city that I allow pets bc I know those tenants will be required to clean up after them per city laws.

We rent single family homes, so we have a conversation about yard maintenance, snow removal etc - have you don't this before, do you have the tools etcI also bring up house cleaning questions, by telling them we had a tenant who did not own a vacuum cleaner, did not know how to run a dishwasher, had a mess in the basement etc - and then see how they respond.That is a non-offensive way to talk about house cleaning and you'd be surprised how different the responses are.