It is 5 minutes from the ocean and is in a small community that is nestled in a valley between the mountains that meet the shoreline.

If they don't meet your standards don't rent to them.

In addition to those I would also suggest making a commitment to going to local meet ups and networking events in your area.

After putting about $50k into the property,  I’m just about $25k from meeting my completion goal that includes stucco, drywall, and siding.

Would be great to reconfigure the lot lines on the two additional parcels so they'd both meet the minimum to build.

Your specific variable expense assumptions are wrong, BUT you stumbled into them being correct overall.Also, you are approaching this correctly - entering in the numbers to generate a purchase price that meets your metrics:)

I would look at their policies and make sure both the coverage and deductibles meet your needs. 

I’d recommend listening to the straight up Chicago investor podcast for local information, going to the variety of meetups that are in this great city, and meeting a lot of the people posting here. 

Not worth time & effort to go to court, your first meeting with an attorney will cost you as much as the rent.

This being said, I don't believe we'll be able to meet the income requirements to qualify for a conventional.This leads me to believe hard money or private lender is more the only option to get my foot in the door, use my business to make repairs at very good rates, build some equity then refi once the balloon is due.