I recommend those that are high income earners focus on making as much money from their job and then devote time to make sure their investments will be good.Spend time analyzing market that you want to invest inSpend time analyzing the PM company.Spend time analyzing the real estate agent that you will work with.Make sure the professionals you work with have proper certifications and experience.Best of luck

How much effort/time does an STR require to operate, and am I willing to devote these resources to it?

The only issue I see with being a realtor and loan officer at the same time is that to be successful you need to devote your time 110% to one or the other.I have known many people who have gotten both licenses and tried to juggle both sides.

and I dont have a day job, but ever since I hired a property manager to devote my time to this, I have too much time , so I actually have been applying for jobs, but theres a reason I dont have a day job, I am a felon, just about makes my degree useless :/ but I am humble, I might not be able to get the 60-80k salary job and might have to take a lower level job, Ive never had a job job like that, so I think it will be a fun experience, have co workers, work friends, maybe find a good woman.

My 2 pennies:(1) I would suggest joining brew city group on facebook along with some other RE groups targeting mke area. (2) connect with other out of state investors in mke area and see what their challenges have been. (3) Linking with the right Realtor &/OR Management company is the key & they can pinpoint "lucrative" area based on your investment expectations & tolerance for risk. (4) Visit Milwaukee & Drive the neighborhoods you are considering so you can be more devoted to your investment (stay away from tough areas unless you are a seasoned investor). 

You specifically said before that you devoted ALL of your free time, then say that's 8hrs per week????? 

Some areas may have an office specifically devoted to tax sale. 

@Alex Ng Because I have worked with my contractor for about 20 years now in some form or fashion( he started out shoveling my roof), he usually walks all of the properties I look at on my initial visits and gives me a rough estimate on cost of rehab and a time frame for completion based on his current schedule and how much time he has to devote to the project.

I do this part time, but hope to grow my business and eventually invest full time, or at least much more time than I'm able to devote now (I'm a mechanical engineer by day).

I have a niche area of commercial that I would rather devote that time to and even that has gotten hyper competitive.