Software like Privy or yours (like we discussed a few months ago) can detect if the house is flipped or not, based on the picture or recent data.I think something like Tableau now should have something like automatic prediction when you feed your data to them.

So a three bedroom home could safely house seven people. 

I've had this situation before and it can work out well when you and the tenant agree to a payment plan, especially when the funds can come out of their account automatically.  

If you have extra taxes then you should absolutely account for them.Contact Vrbo, Airbnb and your local authority and see if they are automatically taken out or if you need to submit the extra taxes.

In my case, seven or eight out of the ten property managers I asked described the same properties.

It also allows tenants to set up automatic rent payments, so no more late rents!

People on these mortgages had their payments go up automatically with every interest rate increase and saw cashflow completely wiped out.

Hey @Tom Brown - I'd echo @Paul De Luca and recommend @Samuel Pavlovcik, but also through out @Prashanth Mahakali...both are awesome Chicago architects and good friends.Things have changed with the City of Chicago, but probably not enough...whichever architect you work with just make sure that they are self certified which can drastically speed up the process.What neighborhood is your property in?

Knowing how quickly great deals are bought in this market, speed wins, and after a follow-up showing the next morning, I put in an offer on Friday.

As a passive investor getting a mentor is a cost/benefit decision: money for training, experience, access, and therefore speed.