There could be white ant or drainage or any number of other nasty surprises too, making remote assessment quite inadequate.They're basically asking as-is market value, so that doesn't augur too well as to their motivation.For such a small, boring, old property, I'd probably be Offering LESS than land value.

I have tried to search/call Boston inspectional services and haven't made any progress.

. :) I asked the tenants for specific concerns and have two licensed electricians on their way now where I will meet with each one individually to assess.

Otherwise, in my opinion,  it looks like you are correct in assessing the situation.

You can be hit with an assessment that will wipe out years of profit.

But it goes to show you this definitely NOT risk free.If you are going to play you really want to diversify your risk, either by doing a dozen or so deals and/or partipacting in a fund which gives you exposure to several properties.I'm going into my third year doing this and been pleased, that being said i only has maybe 2 exits and the rest is still in progress but I am getting my monthly/quarterly checks so that's nice!

I am working a full time job while beginning my investing career and I have to get a masters degree to progress in my current job.

I can see that this is already a good step to building a progressive real estate career.  

This cant be good for the roof or the insurance adjuster to actually assess the damage.

Specifically, I would like to know: 1) is my assessment of the code accurate; 2) should I replace and hardwire the smoke alarms; 3) am I required to disclose code violations to the renewing (or existing) tenants; and 4) can you recommend someone to do the work?