can I deduct painting that was done before I have collected rent?
The date you are actually paid the rent is not relevant. Understand that the property is "in service" on the first day a renter "could" have moved in. Generally, that is the day you put the "for rent" sign in the front yard. Doesn't matter if it takes you three months to get a renter either.
Expenses incurred while the property is in service are deductible. So if you claim the painting costs, which is a maintenance expense and you get audited on it, all you have to do is prove the property was in service, and you're fine. Generally, your chances of getting audited on something like that are extremely slim. But not zero.
Now here's my opinion on this, and keep in mind we all know what opinions are like in the sense they hold no weight in legal matters.
It's perfectly feasible to paint the outside of a house while it's in service, and even if there's actually a renter living in it at the time.
Whereas if painting the inside of a house, if vacant at the time, if I was an auditing agent for the IRS you'd have to convince me somehow the house was move in ready without painting. Overall, I would not expect that to be to difficult. This would be a hard call for me personally though, because I'm not well versed in the legal arguments if any, the IRS may use to disallow the expense.
For me, (and this is just me personally) if I doubted the legality of my expense and I could not get a firm commitment backed up with something in writing from a tax professional, I would not claim the expense.
Remember the three golden rules when dealing with the IRS:
1) You are guilty until proven innocent.
2) The burden of proof lies on the accused (that would be you!) and not the accuser.
3) If it's not in writing, then it flat out did not occur.
