Since I am new in the business, could you give me some tip on how you calculate comps and how to come up with accurate MAO?

It will always be a hard choice as to what to do short term, just look at each of those options and calculate the 4 year value of each. 

@Fedor Volkov I'd give this a try to get you in the ballpark. https://smartasset.com/taxes/illinois-property-tax-calculator#cGnEhuCPUN

The taxable gain is calculated as the difference between your net sales price and your adjusted cost basis (original purchase +capital improvements - depreciation).Depending on these factors you could actually have a much larger (or smaller) tax from the sale. 

View report*This link comes directly from our calculators, based on information input by the member who posted.

With the HELOC, be sure to account for the interest payments to calculate the net gain with the new deal all things considered.

When I'm calculating repairs today I estimate what I think it should cost in 2019, then add 50% and hope I can find someone at that price. 

I’d try to do a 5-10 year projection if you can find a calculator for that and see when looks to be the best time to sell, maybe never if the HOA is well run and doesn’t get spend crazy.

Here's your mission, should you choose to accept it.Calculate the following:1 - (Cash flow per month as is times the number of months you've held the property so far) minus the cash you spent on the property = A2 - A divided by your cash flow per year = BA = the total dollars you are at a loss so farB = how many years it will take you until you have recovered all of your cost...and start making a profit.Now, do the same 2 formulas, except this time calculate it as if you bought the properties using only 20% down...instead of 100% down.  

However, from a logical aspect, simply calculate take home return on equity.