I remember back in 2011, I had wished to purchase in JP where I grew up and ended up investing in Dorchester where I could afford. 

Remember if you do… The STRs that win are the ones unlike any in the local market and also give the extra bit more of appeal and experience.

Remember, networking is essential, and continuous learning is a must.

Then remember after 25 years, you will own that house if you buy vs if you rent, you won't be any further along. 

Remember, C/D located properties generally appraise once improved for significantly more than they will actually sell in an arms length transaction so you can go to many C/D neighborhoods, successfully complete the BRRRR method but deal with  all of the operational difficulties of the asset class and then fail to achieve a sale figure remotely close to the favorable appraisal  that allowed for the proceeds to be returned through the refinance. 

Back in the day, late 90’s my first purchase was a combo loan of an interest only ARM (interest rates were high then) at 80% LTV with a second loan loan for another 15% (I think this one was an ARM or fixed, don’t remember) and 5% cash down.  

Just remember: most negative reviews are written by problematic tenants.

#3 is a rule every new real estate investor (and many seasoned, including at times myself) need to remember.

It’s clear that you’re taking the right steps by educating yourself and connecting with others in forums and groups.Keep leveraging the knowledge you’re gaining, and remember that patience and consistency are key.

A big thing to remember now that you are licensed any offer send for yourself needs to disclose you are IL licensed.