I'm assessing another property and it doesn't appear to be as good of a deal ($80k $900/month) but in an area with exciting developments and higher potential for increase in value.

Yes as you are finding out a lot of insurance companies avoid student housing due to the increased risk.

I may be wrong, but determing the value of an asset based on comparable recent sales would give a comparable cap rate, but couldn't the value of a multifamily asset be altered through increasing NOI?

I have been renting a commercial space to my tenants since I purchased my building 3 years ago at the same rate they were paying before. I have recently found that the space they are in is worth significantly more tha...

If we then get in to a late fee situation, I think they should split them with the owner as I recognize they have increased work to collect the rents, but I'm also out funds while waiting on the rent to show up. 

To All, By paying off 2 mortgages worth around $220K, wouldn't I be increasing my home equity and also helping to reduce my debt to income ratio i.e. a factor very critical for getting future mortgages for future rental investments?

Do you expect your family’s income to never increase and them to always need you to give them discounts?

If you plan to increase your portfolio of properties you may want to have a PM Service the property for you.  

I'll defer to our lending gurus to better fill you in on that end of things, but certainly you should look for ones that are in the path of progress, have additional revenue sources (think storage, laundry etc), or potential therefor and/or have scope to add a bedroom or another unit to increase the income.

I'm sure the novelty of living in a tiny house, and the newness of it will increase price, but that's at least where I'd start.