I am wanting to make sure I will be working with a title company that is familiar with wholesale assignment contracts, seller financing, lease with an option to purchase and possibly sandwich leasees with an option to purchase.

Having a reliable local team, including a property manager and a realtor familiar with the market, is the best way to avoid high-crime areas.If you’re leaning towards Richmond or have more questions about the market here, feel free to reach out.

Once you have found a few with good reviews, call them and tell them you are a wholesaler and ask if they are familiar with the process.

Finding good STR's can be a niche market, so it's a good idea to find an agent that is familiar with STR so they can point you in the right direction for zoning, good markets, etc. 

I'm not familiar with your market but $600 should be reasonable.

Sorry if I got that wrong, but I am very familiar with THAT RW. 

My girlfiend and I are looking in La Grange and Brookfield which is not quite as fast west as you, but my aunt lives in Wheaton so I am quite familiar with your area.What's your game plan over the next two years? 

It will familiarize you with the basic terminology and benefits.

Regarding how properties are sold, listed, comp'd, appraised, etc, I'm very familiar(I own 2 STRs and 23 LTRs).

Use tools like AirDNA or Mashvisor to provide market data on projected rental income and occupancy rates, and make sure your lender works with appraisers familiar with short-term rentals.