According to my contractor, the fix to prevent further damage seem to be simple, seal the gap between the trim and window, clean the gutter, and replace the drywall on those areas if needed.

So I will come clean and clear on everything and get straight to the point. 

If you are offering vacation rentals, all the linens need washed after stays, cleaning needs done, trash needs taken out, etc.    

I have been working hard to clean things up but i had my head in the sand for a good many years so it will take a little while to get things back up to my pre-2008 credit score of over 800. 

Take into account: Accounting, Advertising, Cleaning, Insurance, Lawn/Snow, Legal Fees, Maintenance, Cap Exp, Utilities, Taxes.  

I have seen quite a few homes where the iron is in the  ground water , the people have to monthly clean the sump pit with a garden hose .  

If the land is worth 130k based on land comps, and it costs me 20k to remove the junk thats on it (i.e. the house and potentially two decrepit trailers on it), its going to cost me 150k to get to a clean slate - I think its overvalued at that - I really don't understand how its asking the owner to fund my project.

Your time handling reservations, cleaning, maintenance, complaints, etc.

No you will have to clean walls with a degreasing product and then repaint.

Potential risks - incomplete foreclosure.Yes you can buy a property at the tax sale in Jackson County - but to sell it be prepared to find a buyer that will take defective title as that is the only way most title companies will close - some sort of CYA document stating it was acquired via tax sale and might not be 100% clean.