I think the easiest way to figure out if a deal is good is to analyze minimum of 20 deals, put the numbers (cash flow, cash on cash return, IRR, whatever metric you want to focus on) into a spreadsheet, Find the 25th, 50th, 75th percentile of each of those metrics (or use whatever percentiles you want).

Hi @Luis Fernando Botero, as the others have said in the forum, you are probably looking for a DSCR loan.Those are the easiest to use for investment properties.

It is probably the easiest and fastest way possible to get started in real estate.My only advice would be to save faster and start sooner if possible, but being that you are only 21 years old already I think your plan will work out perfectly regardless of moving any faster.Are you planning on moving into Chicago or staying out by Joliet?   

@James Whitehead it is easiest to access the equity in a property when you are living in it, but you do have to qualify for the PITI payment.What is your current mortgage interest rate? 

To limit the tax hit they will take I would like to gift them $30k cash from my savings and $70k cash from my HELOC.

I know it's easiest to pay the fee but I disagree with how the HOA treated me.

I'm buying my mom's house and the appraiser took properties from a year ago... really shafting the value of the home which is bad since I'm looking at the gift of equity potential.

If you're self-managing, easiest to be within a 30 minute drive. 

When looking at those higher-end neighborhoods, the property may not cashflow or it may have minimal cashflow.The easiest way to research the neighborhoods in a particular area is to get in contact with an experienced and knowledgeable investor-friendly agent.You can get their thoughts on the neighborhoods that are hot and which ones to avoid.As you have seen, the higher-quality neighborhoods are higher-priced as well so it may not be the best for an entry investment property.Alternatively, you can look at other markets.

Easiest, cheapest and quickest way to get a run down of Cle is to read The Ultimate Guide to Grading Cleveland Neighborhoods.