Also properties built in the 80s that were considered to be "newer" condos are now having system failures, specifically roofs.

In other words, what are the Subject's characteristics which the market seems to place value on (i.e., specific location, gla size, lot size, specific amenities, remodeled, etc, etc, etc).

There are very specific requirements that must be completed for a legal cellar basement to be rented out.

Cash offer do carry weight as they can close quicker, don't need appraisals etc, but as an agent that works with buyer and sellers, I've seen it many times where a seller will pick a different offer due to some connection to the buyer (ex military, young married couple just starting etc) They want to know its NOT going to an investor specifically. 

I never promoted any specific project in my replies and rest assured I never will, I shared a financing example in the current Tulum market.

If you have specific questions or topics you'd like to discuss, feel free to share, and I'm here to help!

I can't speak to a short term rental in these areas but I do have a few specific areas worth mentioning.New England is a popular destination for skiing.

I would also look at flood zones specifically in and around the Houston area.One of the biggest factors to look at, as mentioned above, is what the houses cost in the neighborhood compared to what they are renting for.

If possible, consulting a local real estate agent or financial advisor can provide personalized advice based on the specific market conditions in Chicago.

Learn the fundamental basics of the entire process including: researching/finding properties in your market, buying it, rehabbing it, selling it (all specific to your market).