the buzzword  is diversification - but with the purchases I made at the time - real estate far outperformed the stock market.  

I am in the process of purchasing my first STR.

The market rent puts all three together at approximately $2900 monthly.Costs behind the acquisition:Property taxes: $5000 yearlyInsurance estimate for all three: $3,300 yearlyC-class properties (not best location, their condition is about average - older properties)Purchase price: $250,000k$15k down and $235k seller financed at 6% interest for 30 years. 5-year PPP.

Also, I know that by law real estate agents have to disclose if things on a property are unpermitted to allow the potential buyers a chance to back out of the purchase if it's too costly & the real estate agent who sold my friend this property didn't say anything about any of the 3 out buildings that are on the property.

I am looking to purchase another primary residence after my 1-year mark however, I was wondering if lenders will be able to use my Airbnb income to help qualify for my next purchase?

Why do you think purchase contracts are so long and have such small print?

The property I’m purchasing currently has a fence on 3 sides, but no gate(s).

I want to purchase out of state for a number of reasons (Landlord/tenant laws, tax purposes, purchase price, cash flow, etc...) 

We purchased it in November 2020 right before the pandemic at a purchase price of $330,000, a 3 bed 2 bath with a detached garage that was converted into a small room.

BUT Your realtor should be a savant at non-conforming spaces- if you look to purchase in Chicago.