Don't hire some mass mail company who prints out letters and sends them.

Community center with pool, tennis, etc - 1min walkSchool district: 5-6-7Driving distances:Costco - 14minWalmart - 10minLakeline shopping mall - 11minAnd to the Tech side of things (big part of my speculation)Apple/Oracle/Accenture/TriNet - 7minElectronic Arts - 5minAmazon - 12minIBM - 12minDell - 14minVisa - 7minFlex - 6minCisco - 6minNvidia - 9minNational Instruments - 11minSamsung - 20min (insanely huge factory)Everyone above are huge huge employers with 100s-1000s of jobs and constantly hiring & expanding.Amazon is expanding to 800 new employees in “The Domain” new offices by 2020.Google expansion downtown Austin - 5000 new people, 800k sqft by 2022And to the best one!

Community center with pool, tennis, etc - 1min walkSchool district: 5-6-7Driving distances:Costco - 14minWalmart - 10minLakeline shopping mall - 11minAnd to the Tech side of things (big part of my speculation)Apple/Oracle/Accenture/TriNet - 7minElectronic Arts - 5minAmazon - 12minIBM - 12minDell - 14minVisa - 7minFlex - 6minCisco - 6minNvidia - 9minNational Instruments - 11minSamsung - 20min (insanely huge factory)Everyone above are huge huge employers with 100s-1000s of jobs and constantly hiring & expanding.Amazon is expanding to 800 new employees in “The Domain” new offices by 2020.Google expansion downtown Austin - 5000 new people, 800k sqft by 2022And to the best one!

A few months ago I hired an agent and we've been in and out of contracts here in Cincinnati, Ohio, where I've lived for 8 years now however I just received news that I will be moving to Chicago with my job in the next two months. 

Do you have any related skills to fix and flipping or are you just going to be hiring it out?

I should have the benefit of getting accurate expense and income data for any real property to validate cap rate and other information.Property management costs are similar to what they are for a SFH (10%/mo + placement fee) until you get to a certain number of units where it then makes sense to hire an employee.Insurance costs will be proportionally more than a SFH/4plex in the area would. e.g.

Follow this rule:  Don't hire a tenant to do work, don't rent to a contractor you hire. 

If the market isn't as hot OR if you don't have time to show the property, do a background check, etc...hire an agent.

If you were hired as a disposition manager for a wholesaling company, but are also a licensed agent, how would you structure your business to best leverage your positions?

Purchasing an investment property increases the level of difficulty of your tax return.Purchasing a house-hack is even more difficult.To make it even more difficult - you plan to make improvements so you have to determine which costs are currently expensed and which are capitalized.Not only have you acquired an investment property but you also acquired a personal residence.As a result, direct expenses towards your investment property and indirect expenses are deductible business expenses that can be used to decrease your net income from rental activities.With all that is said - you are trying to operate a business so I would hire professionals to help you with your tasks.