At a minimum, having viable plans in place for development will make these lots more marketable and valuable to potential builders when we have conversations. 

Don't get me wrong, there are plenty of terrible landlords out there, but deciding that you are victim of life's circumstances certainly won't improve your situation. 

It takes time to develop trust and credibility with potential investors, so don't wait until the last minute.

In a nutshell, IL (where I live) too expensive of a market, but WI, MI, OH etc seems like you’d get more bang for your buck. also,  you can look at a City’s  consolidation plan and what their plans are for development to get a good forecasting of housing booms.

For a more general philosophy on hospitality, especially if you are going into the higher end STR space I would recommend Four Seasons: The Story of a Business Philosophy by Isadore Sharp about the founding and development of the Four Seasons brand. 

@Dmitriy Fomichenko not sure if you were aware, but depending on your income and circumstances, you can convert that money into a Roth IRA, tax free.A friend of mine lives in Washington state (no state income tax) and his taxable income is about $50k a year.

The tenant base is generally 95% single women with 2 to 5 kids and they flat destroy houses, Not on purpose  most of the time but if you have children all below 10 years old they are just brutual on houses even in the best of situations of which single parent with multiple baby daddys is not the best of circumstances.. full stop.

Tons of growth coming all over town with new developments constantly, plus the weather is great 9 months out of the year!

If it is covered it's usually if caused by a covered loss meaning mold develops due to some other covered peril. 

More like  2X to 5X the cash out.. these are done with builder developers on their deals So put out 300k get 300k back in profit plus the interest rate. most small builders/ developers need to have a equity partner so you just do both you lend the money and are the equity partner.. pretty clean..