can you please check these pictures and advice?

Definitely check them out for the Chicago area!

Check out places very well before you buy, looking at costs, checking the place top to bottom, looking up who owned it before, comparing prices in the area, checking out tenants, and looking at the legal stuff.

BamX is a pretty good platform for agents to network with one another, brainstorm ideas, learn about sales & marketing, and much more.If you're on IG, check out @thebrokeagent and @nowbamI am also part of similar private platform for agents nationwide - happy to share more info on that if you're interested!

I have seen they have been pushing RentRedi a lot on the podcasts lately and I fell victim to their marketing tactics and checked them out.They seem to have fairly reasonable plans ($9/month for year plan) and offer a variety of features but I am still confused why someone would pay for property management software when there are so many free alternatives out there. 

Regarding two mortgages, thats a great point and I will check with my lender on that. 

Then I became the guy collecting the check long before the term house hack was coined.

@Christopher Tacchi You will want to check with your currently lender to see if this would be acceptable.

I like when the tenant puts a check in the electrical panel box and landlord picks it up on the first.

I highly recommend you checking out Guesty in the meantime as it sounds like your main issue is scheduling cleaners, when really, there's an easy solution for that.Book Rec: "ClockWork - Design Your Business to Run Itself" - by Mike MichalowiczSide note - Matt I'm jealous of you being in Kihei, I was there a few months this past Spring, beautiful place.