Here are a few simple and free ways to learn: Go to real estate meetup groups, attend open houses and speak with the agent there, inspect FSBOs (for sale by owner), walk your area, and speak to people tending their yards.The idea is to engage with other people and ask, Ask, ASK questions about their experience with the local market.Some other ideas: find a home inspector who will let you tag along in a property inspection, and absorb what they are looking at and why.Your mindset and enthusiasm for learning about real estate will open many doors for you.Good Luck!

Some insurance companies are asking to see the home inspection report in order to give you insurance or to install a $750 water shutoff valve if the home is older than 20 years old.  

Also - I am an out of state investor, generally speaking, how often do you send your tree guy to inspect the trees in your rentals to check if they are ok or need to be cut?

Watch out for the village requirements and make sure your team knows what areas require rental and pre-sale inspections. 

My monthly fees are as follows (handyman inspection $125, Cleaning $270 a turn (I collect this from guest), TAT&GET (collected from guest) Property Taxes, Insurance (I highly recommend you price this out, with hazard I pay $1,200 a year), internet/cable $100, Electricity $300 a month, AOAO dues $900 (association fees are increasing minimum 5% a year).  

A home inspection produced 50 issues that needed attention.

IF you were to renovate a non-conforming unit, that unit would now need to be brought up to code.When or if you rent out the unit, you, of course, run the risk of the tenant calling the city and saying the property isn't up to code, which would, in turn, cause an inspection by the city and likely result in some violations that would require you to bring the unit up to code.These types of units are ALL OVER the city of Chicago and be rented out on a daily basis, but there is still clear risk associated with renting them out.

I even called the number at the end of the webinar to ask how earnest money works, which they claim they pay upon completion of inspection.

Initially they balked, but eventually they relented* We kept our inspection contingency to void (not negotiate), and included a financing contingencyHow did you finance this deal?

NOTE:  there may be some tax on interest or principal on the payments--seek professional advice.Also, stress there will be no inspections or other contingencies--sell the 'peace of mind' side of the equation.You have known each other for 12 years and you established you are a great payer.