If you wanted to rent it for 3-6 months at a time, you may have to try to time that with the season as non "snow bird" times of year see more 3-7 night stays. 

Unfortunately, winter is notoriously slow rental season in Chicago. 

This could be a seasonal variable where very few families move in winter, but I have never had vacancy this time of year and can't tell. 

Any suggestions of how you think new investors can help out seasoned veterans?

But they're building new houses as fast af people are selling older homes.

The value of this home now is about 85K, considering that it is an older manufactured (even though it looks great inside), and the neighborhood isn't the very best, but we also have had no issues here with any of the neighbors.

Older house but fully renovated in 2016 besides plumbing (I need to check on plumbing health).Home 2 - We are occupying costing us $1700/mo, estimated value is $315k with $250k left on the 30yr mortgage.

@Mahauijue Mack depends what is the refinance for, for rate & term you can refi anytime, for cash out is yiu need 6 mo seasoning in order to use the new appraised value.

Purchase price: $72,500 1200 SF Craftsman bungalow, built in 1930, with an over the garage (450 SF) apartment behind it, on large lot, close to downtown, in a desirable, older neighborhood.

So this is what Im thinking the neighborhood value is on the lower hundreds side( alot of older homes in this specific area most properties are rented out).