I do have another one that cash flows $250/month so it doesn't sting as bad I guess

Get actual estimates on the work that needs to be performed.

If you rentals/properties bump up in the next few years I would take to that person about actually joining your team as your sole handyman for everything, then pay them a salary with you paying upfront for all the materials instead of it coming out of their pocket prior to getting paid back.

With such things, they will usually offer you some time (we had a case once where it took us a while to find a new bank to refinance shortly after the financial crisis in 2008) before actually foreclosing, but they will eventually pull the trigger and begin foreclosure proceedings.

There are no data points for feeling safe walking in a neighborhood (crime per block is closest), local restaurants (walkability scores are great), capital pouring in the area, etc, like actually driving a neighborhood and/or area

Also, I am not in Cambridge - I did not have the option to put the actual town where I am looking. 

In Arizona in order to sell a business you need a RE license just like you do to sell RE, so I am guessing that you could do wholesaling the way you would in RE. 

I guess I should make an offer with her if the property was seen with her in the past, right?

All the great development that actually brings profits (any) are very private and exclusive to big investors.

Please tell me how wrong I am. yes you could, i think everyone in hawaii from mainland is doing this only and it's actually "breakeven" enough.