Does it make sense to finance it over 30 years to increase cashflow? 

Population decline or increase in that sub market?

Financially it would be better to remain renting your primary residence and concentrate on purchasing investment properties.Better yet buy a multi unit and live in one unit while upgrading it to increase rents and cash flow..

)    - you will need to get licensed    - the insurance costs for the building will likely increase    - the insurance for an Adult Day care will be more than a retail business in that space

The main thing is finding a good deal and creating enough value in some way to warrant the increase.

My goal is to increase rental income so that I can hopefully retire in 5-10 years.

Home prices in eastern MA have continued to climb, and now interest rates are as well - and the Fed has said that they plan 3 rate increases next year. 

I understand the principle but in almost every case, the property was bought for $X, was immidiately worth $X + 15%, then a mere 6 months later there majically appeared an incremental 20% property value increase.

I can understand a lender not wanting to get into a third position as the LTV increases. 

As of  Jan 1st 2019 I have raised the rent for both of the 1 bedrooms from $625/month to $685 One of the tenants did balk but they paid it because that is still under value by about $50-60 The garage rent has been raised to $140 from $100 The renter of the garage made no issue of the rent increase.