The bad news for America is that the NIMBYism and hypocrisy of a city like Boston imposing rent rent controls, instead of addressing the heart of the problem through zoning (where it will jab at the lifestyles of the wealthy homeowners of it's population) is never going away. 

SFR, its totally up to your preference and desired lifestyle.

Job growth, population growth, rent growth, industry diversification, income growth, low crime, and lifestyle. 

Just to keep up with lifestyle and bills, I’ve been cutting back, recently.I for the time being don’t see myself moving because I’ve made a life here, my wife’s family is here , her friends her nursing job, not that I haven’t considered it further down the line, I originally came up to Alaska for the money I wasn’t making in Florida. 

Such improvements can significantly enhance your property's appraisal value.For the roof, consider setting aside a fraction of each paycheck for maintenance.

We are on their maintenance requests immediately but we explain that cosmetics, improvements, and enhancements are done when our properties are empty. 

@Andrew FondenI definitely love the smaller more close knit environment you speak of and the opportunity to be more involved enhancing my learning and experience.

We'll be planning to live there ~6 months of the year and rent out the house when we're not there for $150-$200/night, so it's both a lifestyle investment and something that will eventually cash flow very well for us.We have 75% of the cash needed for our first phase (1 bed/1 bath, 1400 sq ft.) and are confidently proceeding with the first phase, but we'd like to build the second phase as well as this will increase the nightly rate we can charge to $400/night and will turn the house into a comfortable 2500 sq ft. 3 bed/3 bath.What are some creative financing strategies others have used to finance construction like this?

You cannot expect those who live in a class D lifestyle to begin to know what class C or B tenants behave as.

We have been trying to figure out the best way to enhance it but thought the cabinet/storage space would be appealing to guests.