I generally agree that buying SFH as first investment is an easy way to test the waters; however, if you’re set on REI I suggest buying a duplex or quad.

If you pick a random OOS city to buy in, based on numbers an agent or wholesaler is telling you or "it's a great market to invest in" and don't know the area, prepare to have lots of cash reserves and to lose money especially Class C. - what's a great market to invest in for one person isn't for another investor.

I usually talk to a dozen banks when preparing to make an offer or just get a property under contract. 8 unit is just south of 20 by the fairgrounds.

@Clare Pitcher we do 12+ month leases to avoid vacancies Nov-Feb.If we take over an occupied property, evict or have tenancy-abandon a property, we first let the owner know finding a tenant will take longer than "normal".This opens up owners to understanding they may need to:1) Offer 3D tour and floor plans to stand out2) Price more aggressively or be prepared for aggressive price reductions3) Offer MoveIn Specials:- NOTE: we do NOT recommend offering a month of free rent that can be used at MoveIn.

Be prepared for trial runs with several different candidates if you choose to hire a handyman to make sure they turn out to be qualified and dependable.

As you speak with prospective guests, just ask them and do some QA testing.

You'll have to get a contract prepared by an attorney.

It was a test, sounds like not a successful one.

. - You've got some pretty solid information above and concurrence that it shouldn't cost nearly as much as you thought, but on a separate note, I'd like to understand your situation a bit better.You are currently just looking for a Chicago property to purchase and asking the quit claim question in preparation for closing? 

One thing I'm trying to do is to test different cover photos to see which ones draw a greater % of click-thrus (which seems like a reasonable thing to test).I'd like to be able to view the Airbnb stats to see, for each cover photo I test, things like what % of people click through on it.