@Elizabeth Kness this situation is quite common and is normally resolved by a letter from the owner of your primary residence stating that you have been and will be living rent free.

You can shop for insurance and find cheaper if possible, but so far, your PITI is the biggest part of your fixed cash flow (you don't consider mortgage payment as expense, only interest part of it).If you don't have any deposits from Rent  at all every month, you need to discuss it with the PM: maybe outsource turnovers or DIY - $4K  per unit sounds high...but I'm not in Chicago...maybe it's normal thereAfter all, you're in this business to make money, not improve the building endlessly. 1.2% or more - if nothing left in your pocket, it's as good as 0%

I have a two flat with a 5 car garage in Rogers Park and I'm looking for a reliable/trustworthy handyman to do small repairs around the place. 

Don’t know that I’ve noticed it, but it’s just stating the normal state law.

Normal comps for move in ready of this size and location are $70-$75/sq ft and rehabs are $30-$45/ sq ft depending on condition.

@Travis Walker I agree with @Simon W. see what you can afford. but to answer your question simply, i was also in debt with student loans, car, etc and i chose to invest in real estate anyway. yes its a risk but if i waited till im debt free id be waiting forever because its always hard to take the leap. with real estate on the side, i paid off my debt a lot faster.

Similar to how you can only sell X number of cars per year without being a dealer.  

I normally think long term is lower risk (occupancy, crazy renters, etc) but less margin when compared to short term. 

It is like a used car, once a new one is purchased, the value of the home goes down immediately.

Set the tone for the showing before they even get out of the car.