If the tenant exercises the option to renew for another 5 years, is there a commission to be paid then?

However, most of the offer is usually low balling due to the price that i want to pay with my calculation.

It's easy to fall into analysis paralysis but remember that your first deal doesn't need to be a home run - if it gives you confidence and gets the ball rolling then that's all you can ask for.Best of luck!

The best you can probably hope for is to find a diversified set of investments that will outpace inflation or to settle on some real assets you think will do favorably according to your crystal ball. 

This is a beautiful/safe neighborhood (lots of families/couples exercising and walking their dogs all the time, etc).

Any personal success stories low balling HUD?

Cost of playing ball in SDIRA world I guess.

I wish I had a crystal ball, but the best thing I've got is what I see going on in the market and my gut.

There is a relatively small risk that Freddie could exercise the "due on sale" clause if you moved title.

I'm currently under contract (my first ever purchase) on a 2 unit + garden in Irving Park, hoping to close next week and would like to get the ball rolling on work ASAP to get the vacant units on the market by 10/1 ideally.