I've successfully completed a few house hacks in California, and am looking into branching out to the Midwest with small to mid multi-family to scale a bit faster.

Here is a list of potential options:Trello/Asana/Zoho Projects/Freedcamp/Basecamp/Workfront/Monday.com/Jira/etc,etc,etc,etc,etc - General project management software that includes tasks, Gantt scheduling, calendars, project forums, document storage & team collaboration toolsTeamGantt/Gantter/MS Project - Gantt Scheduling Softwares for creating Gantt Charts & Timelines, & managing tasks.Podio - Customizable system that allows you to build workflows, track tasks, track leads, etc.Smartsheet/AirTable - Provide spreadsheet style platforms with additional functionalities for uploading documents/images, assigning tasks, calendar, images, etcOffice 365/Google Sheets Spreadsheets - Believe it or not, a lot of successful flippers still manage their entire business in Microsoft Excel or Google Sheets. 

So if a 100% cash transaction doesn't make sense just have the partner who is easier to underwrite get the conventional loan.   

Some use very specific goal setting metrics, some use more general goals, there is no right answer for every person, but I am willing to bet that those that set some goals will be more successful in the upcoming year than those that do not. 

This treatment ensures accurate financial and tax reporting, as the credit is part of the sale transaction rather than income.This post does not create a CPA-Client relationship.

You do that and success will be inevitable. 

Your chance of success is much higher that way.

Follow up with sellers and buyers regularly to stay top-of-mind.By following these five rules, you can minimize most of the common challenges wholesalers face and set yourself up for success.

Although management has always been the key to success or failure. 

There are a lot of variables to consider so it's impossible to say if investing in one of those other markets would have been "better".However, I think you could make a stronger case that you have been (or would be) more successful with your real estate investing in Chicago compared to other markets.