This is my first experience as a landlord, and what a headache this one tenant has been.When the lease with a pair of tenants renting our condo lapsed, they never informed me that they desired an initial inspection, despite my offering of it to them in writing with about 45 days left on the lease.After they vacated, I had a brief list of things that needed to be addressed:The condo was much dirtier than when I initially handed it over to them (I hired a cleaning service to do a 'move-in' cleaning of the empty unit before they moved in).There was a nickel-sized hole punched through one of my floorboards with some kind of cheap resin patch job done to address it, this looked like someone jumped on a couch and put the foot through the boardThe carpets in both bedrooms where pretty dirty; not vacuumed and had an off smell to them.

If you don't do it this year, make sure to patch anywhere that is really bad until you can do it.As for the windows, I would not do all 30 at once, but spread them out over time.

@Bill Gulley is probably right about this being a patch job.

We view this property as an ideal first home for a young family with one or two children.Comparable properties in the neighborhood range from $120k-$150K in 2010/2011 to $130K-$165K, and averaged $88/SqFt per sold home over that period.Needs: 1.New Roof - $7000-$10,0002.New Windows - $4000-$60003.Kitchen/Wall Removal (bigger eat-in kitchen) - $6000-$10,0004.Upstairs Bathroom (gut/replace) - $2500-$40005.Update Electrical - $1000-$30006.Patch/Paint Throughout - $1000-$25007.Update Front Porch (Curb Appeal) - $1000-$20008.Floors (Sand/Stain Downstairs) - $1000-$15009.Floors (Replace Upstairs) - $1500-$2500Addition: (6’x15’ Mudroom/Laundry/Half Bath off rear of house) This addition would help attract absolute top dollar by providing space for a first floor laundry room, an additional first floor half bath, and mudroom at rear entrance from garage.

It is the classic Arizona "low maintenance" lawn style: patches of grass, mostly weeds, and lots of very dry dirt. 

Any electrical also has to be replaced.With Burn houses I was told there was a certain percentage of burn through when framing had to be replaced vs. just patched.

Maybe it's bad form to reply to my own message, but for anyone that's interested that didn't know the answer, I did some more research and found out this is actually a really complicated question.The general consensus of most of the landlording tax books I've looked at says that patching a roof or replacing a section of the roof can be deducted in the same year as a repair.

Get your roof fixed..not patched.

But I can't think of a nicer place to live.The Billings downturn in the oil patch has only affected those who manage operations in ND and WY or who commute there to work.

@Dmitriy Fomichenko Can a self-directed solo 401k be used for investment in crowd funding sites like Realty Shares or Patch of Land?