I might structure the conversation as follows:
"Hi tenant. I hear your concerns about the drafty windows and x, y, z. I would love to help improve things. However, with the current rate of rent that you are at, I won't have accrued enough in the budget to apply these upgrades that you've requested. If we can adjust your rent, I can make these upgrades happen faster as I will have accrued more for just such occasions. I think a $200 increase bringing you to a grand total of x/month would allow me to make these upgrades by y date. Without the increase, I think we won't have enough set aside in the budget to make these upgrades until date z. I'll leave the decision up to you. Let me know what you decide."
I'm a huge fan of controlling the structure and allowing the tenant to make the decision. Once they've made the decision and they try to come back and complain, you get to say "I left the decision up to you". I have yet to have this not work.
I'm sure this will go smoothly. Congrats on the new property!!!