This leads to the main point of this post which I hope results in hearing other's point of views on the subject.  

Long Distance Real Estate investing my David Greene is the best book out there on this subject.

Knowing that I wasn't receiving much value for what I was paying, I decided to conduct research and see what else was out there that could provide most of what I needed at acceptable pricing (subjective, I know).

I am ready for any advice and tips from everyone.Thank youAnHave you thought about doing creative financing or subject to deals?

Short-term rental is any rental less than 30 days and is subject to the primary residence rule and require a permit.

Reason being for it is that insurance companies are getting tighter and tighter, and having a claim on your home can prevent you from getting further policies in the future and subject to much higher rates. 

But if you are doing seller financing on assets you acquired in the last few years and did a cost segregation study, it is something to be cognizant of.There is also "1250 recapture" which is taxed as Ordinary income as well, and is not subject to installment reporting - this is when you took accelerated depreciation (bonus) on any real property assets. 

Does anyone have experience with Subject-To deals in Chicago?

When flipping however, if you do more than one or two per year it is likely that the flipping activity will be considered an active business and incomes and gains from that would be subject to Unrelated Business Income Tax.

It can be quite subjective but based on our past experiences it has worked for us.