I would probably run some kind of vinyl J channel at the windows and doors so as to keep kids from cutting their selves on the trim outs. 

The trim I originally wanted was too expensive and would take weeks so I settle on some cheap stuff that doesn't really match the style of home but whatever, I need to get this done.

I would try to work with the tenant and make a payment plan to get the higher deposit or increase the rent to market value (If your market support it) and not asking for extra deposit.I have a 7 month old puppy in my own house and when she was younger she did some damage (Chew some drywall and trim (But she's still cute :) )) but she grew out of that phase.

Since its a gut rehab down to the studs, it requires new plumbing, electric, some new framing, roof, floors, windows, doors, paint, trim, insulation, drywall, recessed lights, kitchen, 2 small decks, garage door, porch repair, re-concreting driveway, landscaping front yard and back yard (very small lot 2,200 sq ft).

I've only done 30 year mortgages for now, but plan to trim that down to 15 yr mortgages as I have more funds become available and get older.

@Zach BallouDid you think about electric fire place...low cost and easy to install I know they look a bit modern but can install a nice mantel and some decorative trims around if needed or even some leadger stone panels from floor to ceiling surronding the fireplace would be an option also.Search ebay for electric fireplace for better idea.Good luck

More so since Foxconn was announced...the forestry department actually trimmed the trees down the streets so it doesn't look like an overgrown, forgotten area! 

Cut the grass, trim that huge bush/tree in the front, put a couple flowers in pots near entry. 

Install new baseboards, trim molding in entire property as needed.

In fact when a contractor we found finished the amazing trim work he did in our addition my wife tipped him $400.