Look at historical data to determine markets that are more volitile. 

Tough to put lots of money out without good data points.  

I don't know much about the Chicago area but for a SFH fix & flip, a few things come to mind:Look for properties that are in historically appreciating areas.  

Real estate has highs and lows but historically it has better returns than other investments including stocks and mutual funds. 

Those tasks can be done in a morning or afternoon if you have all your data handy. 

Get two or even three other bids ands and that will give you you the data to answer your question. 

Through research we started learning that a portfolio loan with a cash out refinance would be ideal for a number of reasons:1- Interest are historically low 2- 4 homes had a 15-year mortgage (great for a good interest rate but were killing cashflow)3- Cash out- ability to pull out $264,000 to reinvest in more properties4- 4.7% interest rate on a 4.7M loan5- Non-recourse* In my opinion, 1-4 are a nice to have but number 5 was necessary for us to continue to scale.

Switching to a new software is very time-consuming and there's high risk of losing data.

They will expect that you can provide them with detailed information on all of the deals you've done up to this point and that it lives in some type of secure data room (e.g., DocSend, Interlinks, Dropbox) that you can promptly give them access to. 

@Theresa Harris That’s a good data point thank you.