I would like the budget to be around 300,000 the max preferably cheaper if possible.

You want to break down your preference in regard to sale price, down payment, program, (SFR/MFH), seasoning is important, and the two R's you want to pay most attention to is the Renovate and Refinance.Most investors make the mistake on the renovate or refinance and sometimes both.You also have to figure out if your buying as a Primary or investment because if you buy as a primary you always refinance before you rent. 

I live in River North and preferably would like to work in downtown Chicago and surrounding neighborhoods but open to the suburbs as well.

Preferably more and definitely more in high priced markets. 

A 2-year term works if the buyer is close to mortgage readiness and the seller prefers a quick sale.

For lending to friends or family who prefer minimal involvement, provide a **Loan Agreement** with loan details and repayment terms, a **Promissory Note** as a formal repayment promise, a **Security Agreement** if collateral is involved, an **Investment Summary** covering project numbers, process, and security, and a **Disclosure Statement** explaining potential risks.

I prefer to stay on the boat but totally understand the sentiment.  

After he had made the payment to get the property out of foreclosure I had thought he was going to use his original preferred lender to close although took his time and waited.

It’s tempting, but not always profitable.Tip: Stick to improvements that will boost value based on the neighborhood, and avoid unnecessary upgrades.Buyer Preferences: Sometimes, the design or finishes you chose don't match what buyers in that market are looking for.

Modern finishes, Washer and dryer and refrigerator.3bed/2bath minimum is preferred in the Texas Market.If you can add 2 car garage, that will make it more desirable and attach more buyers.All the best