And for roofing, remember that they only pay to replace the roof generally for "moderate hail or severe wind damage." 

There is nothing in place if there is damage from say a car accidentally running into the house, hail damage, someone tripping on the sidewalk, dog bite or if there is major damage to the house that is not fire related. 

There's no free ride in life.

Without replacing the roof, I'd say your two best options are asking for ACV (Actual Cash Value) coverage on the roof, which will only pay a little bit in the event of a claim, or ask for a wind/hail exclusion, which will not pay anything in the event of a claim. 

ride this out and hope this is your worst one ever. 

My target areas are close to any public transportation or anything within a 10$ uber ride from DTSJ.

Put the same amount in every month and ride the highs and lows.

@Ryan Rowe ,  I'd challenge you to consider letting that $10k student loan "ride", and pay it off on the prescribed timeline.Using @Michael Hastings 's 4 points, (and a nod to @Scott Trench 's similar buckets), someone sold on REI is investing in RE in "step3", rather than mutual funds/etc because we think buy/hold real estate can return 10% or 20% on our precious capital, and why settle for less in the conventional investments?

This week I am meeting with him so he can prepare me for a meeting with the manager of his brokerage next week.I am enrolled in a 90-Hour pre-licensing brokerage course I am financially blessed to have a full-ride at Purdue and spent my first year exploring careers (from PT to Primary Education), and am deliberating switching majors (again...) to secondary education with a focus on business teaching, or switch to a business programI have ~$1500 to my name, but have parental support on rent(I'm sure there are other pertinent factors, but really if you have taken the time to consider what I've laid out, you're already too generous with your time, and I reckon those should give you a gist of my endeavors)Thank you so much for any edification you can give to me, I am in full-blown sponge brain mode right now, and the drive is there, so I know "thank you" is read the same by anyone who writes it, but mine encapsulates a lot of gratitude.

They can usually sniff out newbies pretty well so perhaps you can ride off of your coworker's experience or find additional partners who have done multifamily before.All the best!