)    - 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.

It really is best to be on both to increase your exposure.

Since the roof line is kind of funky maybe you can get away with using multiple paint colors on the siding.

The obvious thought is to not claim any as it is my first property and there will be only around $4k in revenue this year anyway but my thought is that I can potentially claim and increase my taxable income which will raise my Debt/Equity ratio in order to purchase another SFH or small MFH next year.