Markets stay flat for five years and you've been bleeding cash then what?

An example of that is tenant must pay for additional electric over flat fee / flat limit since now there is 2 occupants in the home instead of originally one.

Anyone have any experience with placing a flat billboard on the side of a building in Philadelphia? 

Since your lot is already zoned RS3, you can (by right) build a new SFH or 2-flat.

If the area is not growing, then appreciation will be flat.

Doing few roof for single family homes in Houston.

No guaranteed way to stop a determined, experienced thief:(Only deterrents that push them to easier jobs.The roof may be a good idea - until they figure out the just need a ladder to get up there and a rope to lower it down. 

I just bought it in the fall and am trying to complete a bunch of modifications during off-season (e.g. metal roof, certain safety features, treating the deck, possibly updating the fire pit area, etc). 

ie, wind damages the roof and that lets in rain that damages sheetrock, floors, furnishings,...   

Check out this site - https://theluxurypergola.com/blogs/louvered-roof-info/hurric...They cover wind resistant pergolas in general but I would make sure whatever you get will be able to stand up to hurricanes that happen there from time to time.