In the next 4 years my income will drastically increase, but I don’t want to wait 4 years to buy another property that will be an investment.

I don't want to violate any of the self-promotion rules on this thread by specifically linking or name-dropping, but it's from a data analytics platform I am working on specifically built for tracking construction, debt, and ownership activity in the Philadelphia region.I will be posting more detailed insights soon. 

Dealcheck is FREE and it offers an app for calculators.I’m shocked that that your team hasn’t told you how much your ROI would increase and user engagement just by having an app.

You need an income that meets three requirements:Rents increase faster than inflation to offset constantly rising prices.It must be reliable; it continues even during economic downturns.It must last throughout your lifetime.These are all long-term requirements, so the current interest rates are not the major issue.

But ...The first thing I observed was the replacement cost portion of the quote, was, IMO, less than what it will actually cost to demolish the remains of the existing structure, pay for any hazardous waste removal following a catastrophic loss, and actually pay to replace the property in the event of a total loss, even though I used the quote feature to increase the replacement cost value by 20% (the maximum it would allow).

Given that the property was worth $390K in its current condition, I saw an opportunity to make the numbers work while keeping my upfront costs low.Instead of increasing my cash offer, I negotiated a $25K down payment with the seller carrying the balance for two years through owner financing.

If you were able to increase the value of the property significantly after the rehab, then you could bring the deal to a community bank  to refinance and take the hard money lender out.You keep all the equity and don’t have to file a partnership return for your annual tax return, which can be costly.  

These are cheap properties, probably in sketch locations (since that's where cheap properties are) so even a huge increase in appreciation % doesn't translate to a huge change in absolute value.

Chicago is a lower appreciation market but with the trends we've been seeing with increased rates of hurricanes on the east coast and fires in the west, I do think long-term we will see some migration to the Midwest.

You haven't seen it, but you know automatically that that you can increase the rent by $25K a year?