When I do mine, the first things I look for are similar age and sqft. 

It's similar to building a house in that there are many factors that can affect the cost when you're building a website, including but not limited to: > Location and experience of your website designer/engineer (someone in a bigger city with more experience is most likely going to charge more)> Fully-custom build vs. website builder like WordPress or Squarespace> Number of website pages needed (not always a factor, but a website with a Home page, About page, and Contact page takes much less time to build than a website with several pages talking about services, policies, etc) > Number of customizations/extra features (even a website builder like WordPress provides a wide range of custom options)Website prices can end up anywhere between hundreds to thousands of dollars depending on who is building it and what you're asking them to build.

All you're doing is making extra payments now...and adding interest charges. 

There are many companies still moving into the greater Boston area, and many of the dominate industries in Boston continue to require face time - think construction, biotech, education, medical personnel, etc.I do think there will continue to be an increase of people moving from Boston proper into the surrounding greater Boston area. 

Honestly, with an extra $600 per week being provided now, my tenants in Philly will be able to collect up to $1200 per week.

Especially if you and your fiancee are going to be living in it for a couple of years, maybe you could find something that has the potential to add/finish some extra living space in the home.

I'm not always right, but I waded out of a mutual fund as well and the price was down .6% as the market fell over the the remaining hours of trading but I executed the orders at the exact same time.Being able to mid-day trade earned me an extra 3.5% and had less uncertainty. 

Both of our credit is strong 750+ and my spouse has income enough to absorb a good size mortgage but need some extra cash to make the down payment for the second property so was thinking if this was do-able. 

I don't really need to  because the business still generates ample money to pay them and I have some extra personal money (a bank account with 7 million in profits I've made) to keep paying them. 

You should do an analysis like Michael mentioned to look at the annual fees, plus extra tax compliance you'd be taking on by forming an out of state LLC or entity.