Talk to Kris over at Anderson Agency. (812) 887-0443‬We use him for all of our insurance needs.

This would be my 3rd rental property by the way.

Hello @Richard Benjamin Wilhite,We usually do 2-4 weeks before move-in date.We have listed rentals 4-6 weeks in advance as long as the apartment is vacant or the tenant allows regular access (2-3X per week) to show the apartment.All the best!

You may consider mid term rental as that area would support that strategy and you should be able to close that gap of PITI and income. 

I'd like to make some rental friendly upgrades and upgrades In general to my 1910 home but don't know where to start. 

I used to live in northern Illinois, so close to Wisconsin - there are several smaller towns around lakes that would be good for short term rentals. 

If property insurance, it should already be covered by your insurance company and you can ask them to add loss of rental coverage.

Currently the rental income im getting is covering 30% of the monthly motgage payment so i was wondering is that was a good ratio to justify the house hack.

This book got me off the sidelines and in the game: Build a Rental Property Empire by Mark Ferguson and this book elevated my landlording methods: Managing Rental Properties by Heather & Brandon Turner~ Lindsey

if you're hiring a PM - let them handle it for youor, go to a REIA meeting, make friends with a realtor, and ask them to run a CMA for youor - look for other active rentals on a whole bunch of different sites and see what others are listed for