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This story is long but my question is mostly not what to do to fix the problem but rather of how to handle tenants.

When they moved we had one room (small bedroom) that was colder then other rooms. We warned them about this problem but they put kids in this room. Window in this room is relatively new, contractor replaced it 5 years ago, but window is not the best or most expensive. Last winter they supplemented heat with electrical heater ( room is 7X14, not very big ) and we decided to replace radiator. We thought that radiator was the main problem. We replaced radiator this season. Plumber did all calculations and put radiator that is lightly bigger than suggested for this size of the room.

Initially everything was fine. But then they started to complain about heat again. We keep 72 during day and hiked to 75 when they complained. We also checked radiator. Radiator is as hot as other radiators in this apartment! But room is really cooler. They claim that it is 53 during night but of course I did not check the temperature.
We rise heat every day when they complain. It is really hot in our apartment and in apartment on the second floor.
Third floor ( problem apartment ) is slightly cooler but not cold. I have a problem going there with a thermometer. I am afraid it will look like I do not believe our tenants and want to start an argument war. My guest it is around 69-70 degrees. But small bedroom is colder. We are not going to argue on that, we are looking for a solution.

I do not want to fight with my tenants, I completely understand that she want her kids to be warm. I suggested to go and insulate window. They put plastic on window but did not do a good job. I made an appointment to do this but then I had to cancel: I had to take my daughter to the doctor instead of sending her to school and then school break started. I promised to do this next Monday when my child will be back to school. But I understand that problem may be much deeper and insulating window is not going to fix it. May be we will have to insulate roof.
Also, we replaced front side windows in each apartment this fall. New windows are Marvin and suppose to be very efficient. So, as you see we are working on this.

But since I canceled my “insulation appointment” last Tuesday I got calls every day to rise heat. We keep now heat at 74-76 with thermostat in our apartment. I spent several late hours at night during this week in second floor apartment staining new windows ( as tenants went on vacation) and it was very hot on a second floor.

Finally today I gave up and after I got call from my 3rd floor tenant again to raise heat ( it was 73 degrees on my thermostat) and I softly suggested that they can sometimes use space heater.
I told her that we are really looking at solution, that I will go and insulate her window next Monday and my plumber is going to come over that Monday ( I made an appointment already) but I really overheat the whole house because of this small room ( other room in her apartment are just fine). I told her that I hiked heat to 76 now but may be she should consider using space heater from time to time.

She is not the nicest person to deal with. Last year, when she complained about heat and that she has a cold we did what we could rising heat and I brought her herbal tea. Several days later I was cleaning stairs and I found this box of tea thrown in a hallway.

This time she was not very nice either. She told me that she is not going to use space heater again. She told me that she spent extra $200 each months last year on electricity ( I do not know, we used to have all electrical heat in out former place and it cost us about $400 to heat triplex completely, including hot water and cooking during winter monthly. She had to warm up just one small room in addition to regular if not adequate heat.)

She complained that her children are thick from cold. I was very tempted to mention that it is not fair to blame low heat in apartment if toddlers do not wear hats outside. I could only imagine where our conversation would go after that, so, I kept it to myself.

She told me that she is not going to discuss heat problem with me again and she is passing this issue to her husband. He called me after that and wanted to come over to discuss this in person. He will e back from work in an hour.

Now I want your suggestions on how to handle this. I really want to fix this problem. We spent money on radiator replacement, we spent small fortune on new windows. But is this normal to just refuse to use space heater in this room till we find what is wrong? As I mentioned we can do at least something about this next Monday.

What should be my position during this conversation. I am trying to be really nice to my tenants but I had been taken advantage not once because of this.