There are some great neighborhoods here that balance cash flow and appreciation, like Fountain Square and Bates-Hendricks, and parts of Irvington.

It sounds like they covered 1/2 the upgrade.

I wouldn't touch this. 

This will affect things like required down payment, rates, and even which lending institutions would be willing to finance. i encourage you to look up warrantability for financing just so that you don't have surprisses when your 20% down buyer cannot finance that way.

We’re trying to secure coverage for our LLC to protect against situations like missed disclosures during a sale, professional negligence that may affect a future buyer, etc.

If DTI will be the only issue for the rental purchase, a DSCR loan would likely be a good option.

This experience has provided me with a strong foundation in acquisitions, valuations, and deal sourcing.

RI or NH seem like solid options these days as a Boston alternative.

Rockefeller understood the value of real estate, owning landmark properties like Rockefeller Center.

You'll do well if you're this disciplined at 18!