Due to our particular circumstances (including our ages: late 60s), it would be difficult to get a conventional loan to leverage it, and buy more properties. 

After hours (HOURS) on the phone with the IRS, we discovered our accountant, who we fired months ago, neglected to ever actually file them. 

What happens if a tenant destroys the place (not wear damage or neglect).

That being said, the intent to sell the property could change the circumstances substantially.

Am generally not a fan of inheriting tenants and if I do, I prefer that my lease be implemented, but clearl y that is not always realistic.Thank you though for this suggestion and I am going to try to see if working it from your suggested angle will work here in Colorado.In the end, I want to set up a lease that does not have holes, that an attorney, God forbid we ever have to evict (though these tenants do not seem like the type to cause any issues and I generally am a good landlord and stay away as long as you are following policy, so thus having a detailed lease that covers most all and then just backing off.My inspections are generally once a year, outside of the move-in, move out.I also stay very engaged in the running of my property, thus self-managing as in the end, I strive to provide a place I would enjoy living and I actually live on one of my properties.Long story short, don’t care for the very vague lease that the current property management company has running.Additionally I have little confidence in the way they were managing the property.The property has so much potential but has clear signs of neglect and I intend to change that as I never simply abandon my properties.On the question of current lease, I have combed through it repeatedly and do not see any mention of what happens at lease expiration only what happens when tenants are seeking to terminate their lease, “30-day written notice required”.No stipulation on what is required of landlord at end of lease and/or automatic renewal, both items that I cover in my lease and another reason, why am not a big fan of the existing lease.Leaves out a lot.I prefer having systems in place where there is little chance of misunderstanding, so thus the nerves on this one, but I will get through, thanks to you all for all your great advice!

Under different circumstances, the best play is to kick it as deep as possible to pin the other team back.

An LLC may be the perfect route for one person while an S-Corp may be perfect for another.While on the surface, both are doing the same type of business, the facts and circumstances regarding their financial and tax goals, their other sources of income, their tolerance for regulation, their family status and their retirement goals may be vastly different, which would affect the type of entity that works best for them.Taxes are not a cookie cutter, one-size-fits-all topic.

Some areas are coming back where as others are neglected.

If I had a excellent tenant that I had for a year or more I would, under certain circumstance, allow them to do short term rentals.

Once I sold to a friend and used one attorney for the deal, it came back to bite me because the attorney neglected to be sure all the bases where covered to protect me.