My father has been in the lending and banking Industry for 40 years.

The lender at my bank also said he’s starting to see more money being invested in that area and I feel there is a lot of room for growth in that city.Chelsea is a rougher area but flanked by a budding East Boston and a new casino in Medford where people with a lot more money than me are investing in.

What if you come from the mortgage servicing industry, or like a bank.

Banks will always want a personal guarantee from you so there is no real benefit

With a degree in applied mathematics the numbers don’t scare me and I know one day I can get out of the banking industry IT world.At this point I am looking for my first rehab property to fix and flip on the east side and to network with individuals and mentors.

I believe that's a jurisdictional issue. 

I’ve been speaking with multiple banks and credit unions and keep hitting a wall?

Banks will loan at about 1.25.

Do I need to improve the property/raise rents enough over the course of the 2 years that a bank will give me a traditional loan at that point?

I would hit up you local banks, S and Ls.