If any of these properties are near where the one you're looking at is, the value should be pretty similar.For what it's worth, a good quality, finished property on the South Side will generally be valued over $100k (depending on size and bed/bath count).

I am not counting insurance and utilities as a cost as I would be paying them anyways if I were to be renting.

So now I have three painting companies coming by the house to give me a painting quote which is an expense I hadn't counted on.

Buyer's ability to manage the store, store location (demographics, access, traffic counts etc), store upkeep, clean environmental reports also play big roles.Unless you have a strong note in all three areas, you will likely not be able to sell more than 3 or 4 years worth of payments at a time.Scott

This can be very attractive as it's so much easier.When a trusted person in the public eye takes your money and "invests" it, you are counting on their reputation and belief that, because they are an educator, your money is safe.

Also, there are not many long time local landlords in the Midwest/South that post on BP (not counting turn key salesmen who own, actual real landlords not trying to sell or wholesale properties on BP, just here posting and giving advice).  

Impossible to answer that as costs can vary dramatically depending on price points, area, and items you do or don't select to have.In CA, I typically experience approx 1.25% of sales price for closing costs on exit (not counting agent commissions which are 5%).On purchase, it will also depend on what you negotiate the seller today for, if you intend to flip, you should always choose to purchase a title binder to save title costs on exit.

Does that count?

My social group these days pretty much consists of Harley Owners Group people who are all succesful in what they do and don't need to network for more business or brag or talk shop or do anything but follow our official motto which is "Ride and Have Fun".And while that's our official motto, every year we raise thousands of dollars for worthy causes or individuals in need or we help deliver hundreds of Christmas presents to local kids and that doesn't even count showing up at nursing homes to play bingo or eat ice cream or roar kids around the parking lot at the Ronald McDonald house or, well, the list goes on.What a true blessing it is to be able to give back.So personally, when some cube-dweller figures I've got some kind of easy racket going, or some contractor I hired with a hand-shake rips me off with the final bill because he thinks I print money, or some unemployed carpenter I hired to help him out breaks into my storage shed and steals my stuff because he knows 'all landlords are wealthy', well, I just can't worry about what the people who don't matter to me think.

Nobody counted on all the people economizing by moving back home or finding roomates and housemates, related or not.