But I feel when booking all sorts of things that unanswered bad reviews feel like confessions from the seller/owner/etc. that the review is correct.Some landlords and sellers hire companies to threaten to sue people who leave bad reviews if they can't back up their assertions.

You can do some sourcing yourself through facebook groups, wholesaler email list and and even picking up the phone and cold calling some home owners that may be tired landlords, doesn't owe anything and has built up some equity.With enough volume you should come across some solid deals that are worth closing on by the end of the year as you planned. 

The outcome will depend on the CCRs, local laws, and the willingness of the HOA to fight it.The reality is that for $500 a year, it's probably not worth you having a lawyer look into it unless you can get other landlords together on it.

As for the move-in fee versus security deposit issue, many landlords prefer security deposits for better protection, despite the extra steps required in Illinois.

Most insurance companies are leaving state by state and stopping to offer landlord insurance all together. 

For starters, hire an attorney in Cleveland, not Cincinnati.For awhile they were not doing evictions if landlords didn't get their properties lead certified.

@Heidi JohnsonI use Landlord Studio and like it.

Low property taxes, landlord friendly, weather is reasonable, close to Lake Tahoe and lots of enjoyable areas in CA, strong appreciation, strong rents, population growth, diversified job growth, limited land allows for significant appreciation outlook over time. 

Also, what are you doing to make sure you are speaking to the actual landlord and not an applicant's friend posing as their landlord?

Research local property values, rent-to-price ratios, and local landlord laws.