We are going to get an appraisal soon, but based on real estate agents evaluation and comps, we are looking at ~$500k as a current value. 

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provides support for the property tax appeals process.

I am based out of Rock County and often come up to Madison.

Of course the above 2 points can vary deal by deal based on the deal terms, but 99.99% of cases align with the above.

Also curious based on the rent rolls, but as you stated, when new the rents were high but as your multi gets older the rents drop due to more competition.

Always be willing to walk away, or, if you really want it you're going to likely pay above what makes the most financial sense to you based on pure math. 

You need to develop a base of knowledge.  

This is going to sound sacrilege but I think you should get a W-2 job in real estate based on your end game of wanting to be a developer I would look to work for developers, custom builders, surveyors etc.

Hi Shane, I want to tell you something from my research because it seems that we've been doing the same thing when it comes to educating ourselves on RE.Given that you already have 20k, which is around half of the down payment, try to leverage family and friends as private money lender in order to complete the down payment.Second, depending on how long you had your primary, assuming that you did not cash out anything from the equity, you can try out this option ( no need to cash out all, just cash out the amount that you need to make this deal happen).just my humble opinion based on what I have learned!

Immediately if you want leverage to be based off purchase price + verified rehab. 3 months if you want leverage to be based off new appraised value.