That attracts moisture and vermin.

Search for your local or regional conference.Your goal here is to meet as many people as you can, and gently let them know you are seeking a position with a real estate development company, and ask if they might know of anyone.

Do you think it would behoove us to pay the additional 2k up front, make this property cash flow roughly $125/month better, but forgo the potential benefit of having that tax deduction (to anyone who responds, I'm not very tax savvy, so please be gentle with your responses to this), or should we keep the mortgage insurance as this tax deduction might be beneficial.  

Your gentle prodding will get the job done. 

For example, there is no insulation under the floor or around pipes, part of the roof needs repair and half of it appears to have 3 layers of roofing material, single pane windows presenting a moisture problem, some failing siding, etc. 

Lack of ventilation allows for the moisture to build.

But it's not cheap, and I don't think you really need it unless you're having a significant moisture problem. 

flood zones....too old....and i want to say underground basement moisture and mold issues. but kinda on the fence w/that one.

I would suggest a kind, gentle talk, wth paper backup (for visiual learners sake) settinng boundaries.

If it is a good home (but not luxury) or low end, you can probably get away with "gently used" appliances but may not get warranties with them.