They're spending tax-payer money, so they'll cut a check without batting an eye.Document condition before and after with photos, inspect regularly, and you should be fine.

I will spend around $5000 - $7000 a year for tax planning and filing.

If I had ten thousand liquid cash to spend, I'd probably do a house hack two-family and obtain an FHA loan with only 3.5% down. 

you are competing against other investors spending thousands or tens of thousands of dollars on marketing every month. 

One thing I did note is my insurance is $3K a year lower due to the monitored fire suppression system in these larger properties versus my smaller properties that sleep 12 or less built close to the same time.As someone who has lived in Illinois twice, the politicians there don't care if people burn as long as they can tax and spend. 

I'd suggest choosing an area that looks like it has potential and then spend your spare time just driving around.

Recognize that going out of state will come with a lot of learning and education; there's a cost for that of your time and if its better served educating out of state or spending it on the property.

It may sound funny to pay a 1031 exchange service to simply receive money for you and spend it for you, but it is essential. 

Most my clients tend to be out of state, high income individuals that are looking for a great return and not looking to spend 200 hrs on the project themselves.  

The foundation is so bad the house has shifted and I’m going to be spending nearly 40-50k to get this remediated.