A lot of this would have been handled a lot better during probate but the attorney was pretty useless and we definitely don’t want to use her for trying to figure this out. 

And like here in the Upper Westside 2-3 years ago neighbors would tell us how much the schools have gotten better. 

I personally welcome the feedback as it can only help me become better at this.I think there needs to be a degree of fairness/ principle here though.

In the residential world, some requirements are relaxed comparing to commercial so it's up to you whether you want to spend the money to have a better planning versus skip the planning and perform the work impromptu.

What's better?

If these are investment properties you are looking to purchase then, DSCR loans may be the better option for you. 

These areas are known for better school districts, less turnover, safer areas, all resulting in better tenants taking care of your investment.

There is no worksheet out there that will tell you whether investment A will be better than Investment B without factoring in risk.Sponsors can inflate the 'projections' to however, they see fit. 

You could probably just do a long term loan instead if the repairs are not heavy with a better rate and fees. 

In this event you will be able to purchase the property for less money now and refinance at a lower rate when interest rates drop, making your deal that much better!