Personally, I would pay the extra interest to have the flexibility associated with the lower payment of the 30 yr.

Tenants are a lower income type of tenant.

Your market - do you end up more profitable if you charge back utilities with a lower rent, or you paying utilities and bump rent payments up.

Are there any real estate syndicators on here who have experience raising money for low risk deals that provide lower returns.

If this number is greater than PITI this lowers your DTI ratio.

I thought I was all set with loan forgiveness based on the original loan origination date, but then I learned that because I consolidated loans a few years after graduating to take advantage of lower rates, the clock restarted.I also learned that the "income based" repayment program is a scam. 

Since I wouldn't be able to access this money till the age of 59 1/2 I am wondering if it would be better for me to lower the amounts that I am putting into these accounts to either put some into index funds or invest in more real estate.

In many cases the adjacent area experiences a halo affect of appreciation because it has similar benefits but at a lower price point.

If you're having the roofers come in after you do the tearoff, make sure the dumpster is there for them as well... they'll have cut pieces of new shingles and similar stuff to get rid of.I have also seen a couple of dumpster companies that offer a lower rate if all you're putting in it is shingles, no general trash - I suspect they are hauling it to either a recycling plant or a construction and demolition landfill, which is cheaper for them than a general-purpose landfill. 

All of these things will likely result in a lower offer being put forth (ie, it doesnt help the listing and sale process).Just my thoughts :)