Its definitely my goal but I fear Boston is at its peak and it won't double in price again in our lifetime. 

I think your creating fear where there shouldn’t be.

As Warren Buffet says, "When everyone is greedy, be fearful; when everyone is fearful, be greedy".

There is no move In check list, so I am afraid if I make them unhappy with all these changes and they decide to leave, they could trash the place and just say everything was like that before (when I toured the home they had already blamed some things on someone else).Is this a valid fear?

My fear is that I'll have to rip up the house and repipe the place when right now it's pulling me in good cash flow and has stable tenants. 

My main goal right now is to get over the initial fear and get my first investment property by end of 2018.

One of our biggest fears is getting into this property and having to throw down another $20-30K in CAPEX within the first 12-18 months.

It just kept my head down and continued working in corporate America coming into work tired everyday fearful of losing my job in order to take care of her.

I did some renovations but not a rehab) and soft details (the struggle with fear). 

Most people are still fearful especially when it comes to the Michigan market which makes it an awesome opportunity to pick up good deals.