I agree with @David Krulac - hopefully your property is in one of the 2% RTT areas rather than one of the 4% or 5% RTT areas.The imputed property value used to determine the RTT amount can be found by taking the tax assessed value from the tax assessor, and multiplying (or dividing) by the common leveling ratio that the PA Department of Revenue has posted at their website, for the year and month of the transfer (the values in their table change over time).Once you have that value, and the tax rate for that location, you can figure out how much this screw up cost you ;)

Not having much information to deal with, it seems that you have a good sense here and it's pricey.  

It does not challenge me or bring me any sense of achievement.

This doesn't make sense to me cause the agents said the insurance policies were bound before cutoff (some insurers were still able to write policies earlier today).With your closings on Sept 19th and 11th of Oct, Irma should have passed.

If it means you loose 1/2 of the amount that was not performed, but you get the rest, do your numbers make sense to move forward if this is the case?

I've been reading everything I can and analyzing deals as soon as something catches my eye, but the only areas around the chicagoland region that make sense with our crazy high taxes for buy and hold seems to be Aurora/Joliet.

It's part of your PITI and should be included as such in your math.Just like a deal might not make sense because someone's FICO yields a higher interest rate, there are also cases where a deal might not make sense because of the high property tax bill, HOA dues, etc.

I find that providing a good product, with quick service when a maintenance request comes in and a sense of respect really goes far with these type of people. 20-30% cap rates with low stress are possible in these areas.

I've analyzed 50+ properties and most of these do not make any sense at current prices.

You could also look into wholesaling, but that's a lot more hands on in the sense you have to really put a lot of time into searching for deals, and networking with people.