I do a combo of short-, mid-, and long term rentals on the northside of Chicago and surround suburbs.

@Matt Schreiberi think the short answer is... no.but... a lot of inputs missing - which market? 

Everything comes with a risk but I want to hear everyone's opinions for both states in the long run, thanks in advance It really depends on your style and goals and type of investing.I invest in multiple states and there can be some substantial differences.First decide if you want to do Flips, Long Term Rentals, Short Term Rentals, Shared Housing, Multi Family, Land, Tax Deeds, REITs, Syndication, Commercial and then decide. 

I have additional questions but am running short of time drafting this post.

Some options that might be viable for you include: Private Lenders – Such investors usually offer short-term lending but provide greater flexibility compared to a traditional hard money lender.Lines of Credit – Another alternative could be an excellent option to finance several deals at once using a business line of credit or HELOC (if it applies).

I am basically shorting the US-dollar.

It's my understanding the Gator Method consists of providing short term loans to cover other investor's earnest money deposits.

I mention all this to in short say, expect very high maintenance on the front end. 

Also, the short answer to your question IMHO is as early you possibly can haha

Some have short learning curves and others have longer learning curves.