If you were looking to withdraw gains then you would be subject to penalties (i.e. if you contributed $6,000 a year ago and the value of that $6,000 is now $6,600, you could withdraw the $6,000 with no penalty but if you wanted to withdraw the remaining $600, then that would be assessed and early-withdrawal penalty).There also shouldn't be any additional tax liability as a Roth account is for contributions that have already been taxed, allowing for tax-free withdrawals. 

I like using the same color because I can just do a light blend coat between the shorter tenants, and frequently don't need to do ceilings, now that I have all the units on this regiment.

subject-to, seller financing, master lease, option to purchase, private loan, partnerships, heloc, credit card......

There is an entire forum on this subject which you can find HEREAlso check out podcast #364

I frequently get bills from him ranging from 50.00 for a minor fix to $1500 for more major items.

I'd like to create systems in these markets to be as hands-off as possible, but at least in the beginning stages, I will be visiting these areas frequently and would like to enjoy it!

You can structure owner finance, lease option, subject to, rent to own etc.

I am looking for an agent that works with investors in the Chicago area frequently who could direct me to a solid lender.

@Kyle NelsonOne thing you might want to take into consideration, whether or not each jurisdiction/city will allow air bnb, or the frequent rentals to multiple different people.

However, landlords who still have a mortgage on the rental unit may be subject to extra restrictions.