If you are just getting started here in Chicago, house hacking is the ideal situation.

@Chad Chase - I think funding a fix and flip with a HELOC from a primary house could work.

Your time is worth money, it's time that guests aren't renting your house. 

Hi Linda,Lots of great advice from @Carla Gordon @Brian Schroeder @Jay Thomas Specifically I think it's always smart to check out FF Traveler sear https://www.furnishedfinder.com/housing/New-York/New-York) and Airbnb/VRBO for 30+ days stays to gauge what sort of similar properties are currently out there!

To set the stage, I'm owner of a short-term rental property in the Poconos in PA and we use a property management company for bookings, maintenance/cleaning, guest management, etc.This past weekend we had a guest booking but when the guests arrived Friday evening the house had no running water, though it had been running fine earlier in the day when the Property manager (PM) was at the house to give a final check and leave the welcome packet.

Flipped a house before?

I believe depreciation on that unit that you were living in starts at that point as well.just bringing this up because it was mentioned in another post where someone was house hacking.

I can't give a tutorial re how to originate a note today, selling a house with financing in just one post. 

I am trying to hire a licensed REA for my LLC to perform occasional open houses and move-in/move-out inspections since I am out-of state from my rental property.I have the REA identified, now I just need to know the steps to creating a contract for them and me to sign.

Alternative route I chose, I will leverage my duplex (purchased 4 years ago) equity through house hacking to have skin in the game on next flip.