Financially it only makes sense to invest remote if you have a sufficiently large economic delta between the market you live/work and Milwaukee.

My goal is to have financial freedom so I can eventually quit my 9-5 job and use my time to spend with family and do things that excite me.

It would be good to talk to a lender to make a game plan and review your financials. 

I'm looking to get their "package" which includes a Holding company, LLC Subsidiary​, Corporate Financial Program and an Estate Plan.

@Rory DarcyRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

We were in a financial position where we could keep our existing home, upgrade, and purchase another home.

To avoid unnecessary liabilities, delaying acceptance or exploring a cash alternative may be the safest financial option.This post does not create a CPA-Client relationship.

Below is some copy & paste info about our methodology:----------------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Do you want your son to bet the financial outcome of his 20s on this seller's ability to make good choices? 

Something I caught within 10 minutes of looking at the financial.