When any damages occur or upgrades are to be done I front all the money, complete the project, and forward receipts to my landlord who in turn cuts me a personal check. 

@Joe Fairless @Brian Burke @Brian Adams @Joel Block 

I put an end to that when 1 woman who complains at least once a week emailed me to ask that I tell the tenants next door to her to pick up the pumpkin that fell off the railing because it was blocking her and her husband from parking their two cars in a 1 car spot.I told her it would be quicker if she just went next door herself and KINDLY asked them to pick up the pumpkin and reminded her she wasn't entitled to having two cars in a spot (one behind the other) when it's technically one space

I have a small portfolio of 3-4 BR townhouses in Baltimore (edge of Charles Village) all located on the same block.

And arguably, when the melting begins, flat roofs are less likely to have mass chunks of snow slide off... common among pitched roofs, and when it happens, gutters are often damaged or torn down and shrubbery and the like below, may also be damaged.

Is there a way to block him all together?

In my opinion by even writing the tag line you have puts a block in your own head that says the odds are stacked against you even more then being young. 

We only received the deposit claim today, so we should be within the 15 day period.The following two paragraphs are the only ones that tackle repairs:"Tenant agrees to take good care of the house and its equipment, or if damaged, other than ordinary wear and tear, Tenant will make repairs and replacement equal in quality to the original construction and if the Landlord makes these repairs, the Tenant agrees to pay cost of same upon presentation of bills.""

My concern is that I will not know about anything that really needs a repair, and more damage will result.

My sister stays like 3 miles from the location and my cousin stay a few blocks.