BTW, I have a great agent, an 800+ credit score, a high paying tech job, no debt besides my mortgage, a home that's difficult to get a HELOC on because appraisers can't figure out what it's worth (I live in the country in a very unique mid century home), but only a small amount of cash.

Some contractors have insurance, some are 1 man band with no overhead, quality of work factors into cost, level of finishes.We created a calculator for our clients to use here in Chicago, specific to our renovation pricing, but even that is just a guess based on some assumptions.If you can find a quality general contractor, pay them like @Bruce Woodruff mentioned, and it will make your life so much easier...you may eat into some of your profits, but being able to rinse and repeat with someone you trust is priceless!

; No water/sewer/storm pond or drain.Segregate the analysis of the house and the storage. 

@Leah MillerTypically no - condo bylaws and zoning regulations typically do not allow to segment a units potential exists to possibly combine units (which can be cost prohibitive as you need board approval and potential building code issues) but I have never seen a condo building allow someone to subdivide a unit

Unfortunately, due to an unforeseen event, me and my friend are no longer able to attend, but our loss could be your gain!

I did read Boston’s ordinance but honestly it made no sense to me.  

The Assisted Living Facility will have insurance and $1M in liability coverage.I called my current insurance and they told me they would no longer cover if I rent to a business like this.

You should definitely not invest here or move here.Trust me, no need to come confirm.

We’re probably the only designers and contractors who would say no—unless you’re in the luxury STR space.Why?

Therefore my only way is to apply to the municipality for an update, I want to explore this option but I have no idea where to start..?