. - I am just a landlord, not a tax professional.

Check with your tax professional about your individual situation and nature of your expenses.

Disclaimer: I am a tax professional, but I'm not your tax professional and don't know all the details of your situation.

Replaced windows in three houses, took quotes, hired contractors, have replaced a few by myself after watching the professionals. 

If it is not your intent to inforce your lease as written you should rewrite your lease.I consider this to be a professional approach to our business.

Just need to keep it professional.

Just consider the money you put in a contribution (rather than a loan), and the money you take out as a distribution (rather than a repayment).Of course, talk with your tax professional first to make sure there isn't an outside detail I am missing that might change this for your situation.

And being a "real estate professional" does come with tax benefits. 

@Ashish AcharyaIf you want to give me a quote for my tax situation; full time IT professional, 4 rental properties, one primary residence.

The juice usually isn't worth the squeeze in situations like this, and the added professional liability, administrative hassle, and paperwork might not be worth it.And remember - Your broker gets his or her usual cut (based on what your agreement with them says), so it may not be worth your time either.