I'm concerned about having my cash "trapped" in the rehab for too long though?

We combined have good incomes but I'm concerned my LLCs will make them think we're too risky (I own 33-55% of four houses and my own house with a renter in my home, all are doing well financially but I ran into this problem of really having to search with getting my own mortgage because they looked at only my percentage of income but all the debt as risk). 

My concerns are: If I buy a place with the intent of renting, are the interest rates and down payments high on home loans?

If your concern is cash flow only, I'd do it for sure and have thought of doing it myself.

my concern is that if they leave in the winter i could be 2-3 months without a new tenant.

My experience has been that new investors have 4 main concerns that have to be resolved before they will invest: 1.

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My main concern is that I will be making about $350,000 profit on sale and not sure how the transferring to an LLC will affect me tax wise.

One of their concern is capital gain tax that they incur due to the sale.

At the same time, IL/Cook is not doing good financially, so I'm sure it'll just go up.Declining population is a concern also.