I give them the option to say no first. my vendor has a radius he will work in. and has a minimum standard of craftsmanship he is will to do.  

Mortgage payments can be lower – and private mortgage insurance removed altogether.Plus, homeowners keep the tax deductions that make owning attractive.Homeowners can use their equity – not borrow against it.

but hadnt been touched since...so the stucco has these disgusting seashell designs on it....The kitchen cabinets,although in good shape,are very dated also...and the windows are double glazed,but they are the original windows from the 70's it looks like.we are both low on money and could probably just afford to fix it up to the standard matt wants to.But what I am trying to convince him to do,is to rent the house out for the winter and save the income from rent (we own the house right out so have no mortgage) then come back to it next summer when we have the rental money and money we have saved and using that money,-put siding on the house.

a deduction is a deduction regardless of the entity you use, but there are arguments for a C corp or a flow through  (S corp or LLC). 

I ask this because if you signed a standard 1 year lease that usually states that rent is due monthly and your picking it up weekly, she might have a point.I would not recommend going to court, but if you are not an LLC or business entity, then why waste the money on a lawyer...just do the eviction yourself (the right legal way).Did you do all the proper things with the security deposit from her? 

Useful life is entirely a tax concept that determines how long you can deduct a given investment in an asset, and has nothing to do with how long something will actually last and be serviceable. 

Is it immediately deductible this year?  

Figure out how much all of your real estate is worth and deduct your mortgages.

The association will have the rights to deduct some type of management fee for their efforts, repair costs, etc. but Yes the collected rent will off set the past and ongoing fees to some extent.  

Peeling paint, ripped screens, bad roof, broken windows, damaged siding, wood rot, chimney falling down, etc. are all things (and more) that they will cite you on.Personally, actually living in Milwaukee, I prefer rental properties to be held to a standard of decency because I don't want rentals dragging down the neighborhood.