hudsomestore.comhomesteps.comauction.comhubzu.comhomepath.comI also pull up foreclosureradar and craigslist as a part of my daily routine.

thank you @Brandon Battle and @Chris Clothier. i am not going turnkey but will be placing property management. the companies i am interviewing are insured and seem to be reputable (most come as recommendations from BP'ers), but it made me raise an eyebrow. appreciate the feedback!

I'm not necessarily relying on refinancing to fund my next deal after this (through a combination of house-hacking in Chicago and being able to routinely save $4-5k/month by doing pretty well at work), but it would be nice to see--and be prepared for--the day when I can build my portfolio with borrowed money vs. waiting until I have a new $20-30k saved up. 

You will be lucky to keep 50% of your rental revenue and, over time, will be lucky to collect 10 months of rental per year as an average.So be prepared to only realize 84% of expected rental income and then will lose 50% of that to taxes, insurance, management, routine maintenance and playing catch up on deferred maintenance.Run your numbers off of those calculations and if you like what you see, then you will at a minimum have a more realistic outlook and expectation going into your investment.I'm not sure there is much difference between the two markets.  

It will only cause issues down the line, as everything is routinely revealed during underwriting and through the various checks done.Certainly if you have a good relationship with the private lender you put yourself in better position to take advantage of any opportunities they may have.

This is usually accomplished with some level of entity layering which can accomplish the desire for liability limitation while not screwing you (or your heirs) completely over from a taxationThe OP was also wondering about holding everything in one S-Corp, which (although I'm not an attorney), I would raise an eyebrow at.  

I routinely use my earned commission % as closing costs or just remove them all together to lower the price.

I will receive no benefits from the increased rents unless I exercise my option to purchase and become the owner.The property manager will not have to change his current routine or job, except for handling increased traffic of new tenants.This plan is beneficial to both of us, because it allows me to minimize the risk involved with purchasing the property, while you enjoy increased rents for a few months.

In my area there are $5-600K tear downs that are routinely bought by cash buyers to throw up a million dollar mansion.

You need to start talking to contractors and getting a general idea for what the $ psf is for various items that routinely need to be fixed.