I'm just trying to prepare for the worst.  

Worst case you get a NO and move on to another property.

or Would I be better served to just shoot him a conservative offer number based on a worst case scenario guestimate of repairs on the one and assume the same condition on the others?

view=item;id=10008 Here in Anchorage they have been working in cleaning up one of the worst areas of town.

If you lose your job and tenants move out, in a worst case scenario you can declare bankruptcy and wipe out the house debt, you cannot wipe out the student loans if they were government insured.

People have developed a sense of when someone isn't telling the whole truth and their mind will start to create the worst possible scenario of why your not being totally honest.

Something to consider.As far as hotels, just go to yelp in the area you want to invest in and find the hotels with the worst ratings.

Assuming a scale for A being Best and D being the worst neighborhoodsBuy cash flow properties in ideally B, B- To C+, C areas with good economics jobs etc.So if someone says they need $ 8000 in cash flow per monthWe would build the model as follows.

@Alan PedersonThe worst of your situation is that based on your mortgage payments and rents all your properties have zero to negative cash flow long term.

You won't hurt their feelings.Also, finding a random agent on Zillow, especially if you need an investor-friendly agent, is probably the worst way of finding an agent.