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

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. 

Consider alternative financing options like portfolio loans that leverage your overall investment portfolio, private money lenders who may be more flexible with income verification, or negotiating seller carry-back financing directly with the seller.

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.

Alternatives to using your cash to buy a Home:S&P 500 Index:Assumption based on history: For the last 100 years this index fund has average annual returns of 10.13%.

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.

Some lenders specialize in working with investors and may be more flexible with credit score requirements for multi-family properties.If traditional lenders are unwilling to approve your loan due to your credit score, consider alternative financing options, such as working with private lenders, seeking seller financing arrangements, or partnering with other investors.

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).