It could end up being a very costly lesson if fines start being assessed.  

Last year's tax assessment was $217,000.

He then demanded a showing and I refused saying it was obvious we would not be compatible.

The right of redemption is limited to (1) sales for unpaid ad valorem taxes, in which case a former owner of homestead or agricultural property has a two-year right of redemption (for commercial properties, the redemption period is 180 days); and (2) HOA foreclosure of an assessment lien, in which case a former owner may redeem no later than the 180th day after notice.The redemption right is the only right retained by the former owner, who is not allowed to occupy, possess, or receive rents from the property during the redemption period.

One thing you always need to be aware of in Baltimore is the insanity of the property taxes ($2.25 per $100) and even the assessment rates.  

The investor is requesting a POF letter and a signed disclosure form before I can even go take a look at the property to make a thorough assessment.

For example, here in Philadelphia owners are required to pay the transfer tax on the assessed value, which amounts to 2% out of your personal name and 2% into your LLC.

Look up the assessed value of both parcels on Chesco's property assessment site and by comparing the relative values, estimate the additional MAO that you would offer for the house with garage. 

Where do you draw the line and how would you recommend assessing neighborhood quality from a distance.

This way you are not putting any assets under anyone but you still get a fair financial assessment / advise.