If you already have a preliminary site layout showing the size and quantity of buildings you can put on the lot, you should be able to take that work on some budget construction costs and from there work your possible rents into the equation to see if what you have drawn makes sense cost wise, or if there is a more efficient way to lay the site out and reduce costs. 

Regarding insurance, i would recommend working with an insurance broker (happy to DM you the one i utilize) and they can shop for the best one for your rental. 

@Stephen FrazierI'm not 100% sure what you're asking, but I would strongly recommend against buying something with 100% financing where part of that financing is a HELOCYou will probably just lose moneyIf the home is owned free and clear, maybe the kids would do seller financing? 

Everyone has their own process, but I recommend starting in excel with a unique ranking system based on the inputs that concern you the most.

I am thinking if there is any online property management that does showings and responds to any maintainence requests?

If you are near the far south side I night be able to recommend someone. 

. - The ability to create online debit cards has helped a couple of times but I'd categorize this as a nice to have. - Free would be nice but if it's paid and has extra functionality I would consider. - Interest earning (not a ****** 0.2% either).

Rents seem to be about as high as they can go for now.

This lead to 3 years of very profitable success as a real estate broker, until having made some highly profitable deals I decided to quit the real estate “business” and concentrate on “investing” full time.Biggest “TAKEAWAY”: Most business owners and most sales people have a hard time turning down ANY piece of business.

I've seen post online that say that Section 8 will help you with the cost to remodel a home if you then place it on the Section 8 program.