All but two of the bedrooms have more of the insulated duct material blocking the entire vent a short distance before the air supply vents, with only a small hole cut out of them--probably 3" by 6" in the bedrooms, and down to about 2x5" in the bathrooms. 

Assuming $2600 rent, with 10% prop-mgmt fee, plus a 15% contingency, that leaves $100/mo cashflow which seems like is cutting it way too closeMy main goal would be to diversify my investments beyond stocks and bonds; also would be good to be able to apply the initial leverage I used during the purchase for a longer period of time for appreciation (not sure if that's sound logic tho); and finally would be nice to not pay the $30-40k in selling closing costs.Thanks in advance!

I recently found out this week that the tenant has not cut the grass in three months and he is still only paying $700 a month.

They focus more on safety and health issues.

The irony of the investment strategy of the average American – including those who meet the definition of an accredited investor – is that the bias toward optimizing for the downstroke and safety robs one from the benefits of individual growth and setting the stage for their future self.

I’ve found that no matter what I do there’s no way to cut costs in my state on a closing and maybe that’s best but it’s around $5,000 every time.

Then he rents the five bedroom house as an STR that covers his mortgage and puts like $6K in his pocket each month.In fact, since you're in medical sales, you might have an edge on finding STR properties that are near hospitals or universities.

Quicken wasn't going to cut it for him. 

if you share a home with your parents and wife, your income (and your wife's) should be able to go a bit further than if you were single or the two of your lived on your own.You were able to save enough money for a down payment on your current home, so do a quick check of your finances and see if you can earn extra income or cut expenses to save for a rental. 

@Sam Collins most brokerages will let you do a personal transaction as an exempt transaction, but if you make a business out of it then most likely they will want a cut of the brokerage side.