I like hearing about the successes and some of the setbacks that were overcome to make real estate investing worthwhile.

There are investors there, as well as people that will sponsor your deals.There are many ways to overcome the cliche' my friend.Do some of the options I mentioned take effort and some money?

This will overcome your lack of ratings which could otherwise be a barrier.

My second question is probably tougher to answer until it's time to apply but I'm curious how holding high reserves relative to the purchase price may overcome spotty employment history. 

I am not familiar with financing and I am still afraid to do it.If I have someone to teach me, make me more confident, I can overcome my fear.

I want to become a big fish / cash buyer, how do you recommend overcoming those cash buyers when I don't yet have the funds to do that myself?

Once you combine selling costs with going from a 4% rate to a 5% rate you have a much higher hurdle to overcome.

i.e. how'd you overcome that initial fear. 

And we have guests from all over, come for all kinds of reasons. 

Greater Boston is a tough market to cashflow but "Persistence overcomes Resistance" as you may have heard.