Read all of this, it contains all the vital info you need to take action:https://www.biggerpockets.com/guideshttps://www.biggerpockets.com/store/flipping-houses-ultimate

I look on Craigslist and other avenues for distressed properties on a regular.

Spray or regular insulation?

Quicken is probably better for a first time home buyer or a regular retail buyer.

You can pay cash for your purchase to give you the competitive edge in purchasing and then roll your buys into either a portfolio loan or regular mortgage. 

The Cook County Human Rights Ordinance: This ordinance prohibits people in Cook County (including employers, landlords, property managers, real estate agents, store and restaurant owners, bankers, lenders and Cook County government officials and employees) from unlawfully discriminating against or harassing other people on the basis of that person's race, color, sex, age, religion, disability, national origin, ancestry, sexual orientation, marital status, parental status, military discharge status, source of income (including use of a housing choice voucher), housing status, or gender identity.

I regularly work with my client's CPA to ensure we are setting everything up properly from a global standpoint. 

We're trying to do the 'right thing' (for us) by catering to this market, but sheesh... it's certainly not like advertising a regular rental.

By that, what I mean is, what data points/sources of data, have you used in the past, or that you currently use, to help you identify a spot in town that is either experiencing gentrification, or is likely to experience gentrification.This isn't question isn't meant to solicit anecdotal/qualitative responses like:"I drive the same road every day and have watched the properties go from being shacks that are barely standing, to getting torn down and replaced by new apartment complexes" -OR- "whenever Starbucks builds a store in an area of town where most of the properties are eyesores, distressed, or are mostly rented out... if Starbucks is building a store in that area, I know it's going to be up-and-coming"That type of advice may be beneficial for some, but much more circumstantial and prone to inaccuracy.

I don't have much to offer in the way of experience yet, but I would say these 2 books have really taught me a lot https://www.biggerpockets.com/store/rental-property-investing-physical https://www.biggerpockets.com/store/brrrr-ultimate .