@Nicole De Lia make sure you use conservative rents, high for repairs and expenses, high on property management and also if your taxes are very low then factor in that your taxes may go up sooner than later.

I got my RE recently and am kicking myself for not doing it sooner.

Well I'm assuming your referring to real estate, otherwise I have lots of strong words about dating and choices in relationships for my younger self........In regards to real estate GO BIGGER SOONER.

While we could potentially save to get a multi-family for investment much sooner with the option 2?

One difference that factors in is the Term length and what happens if the project finishes sooner. 

That will get you to retiring sooner.

Likely $5300 though.Logan square neighborhood: safe, walk able, desirable, close to public transportation, close to restaurants, gyms, etc.

If you're thinking about getting a loan or cash-out, talk to a lender sooner than later!

A notice clause that can be submitted by either party.If you force them into a 12 month lease, they will still leave whenever they want and like mentioned above, you will just chase them in the courts for your money which can be exhausting unless you work with a good collections attorney.If they are not paying on time and are not clean, get them out sooner that later!

I am still learning about REI (a little late to this party, I should've been learning about it much sooner) but it seems like OOS would be our best bet for monthly cash flow.