We went through and had the electrical updated, replaced the furnace with a modern one, put in central AC, a new roof, replaced the windows, updated the plumbing, had all of the old asbestos insulation removed and replaced with modern insulation, put on steel siding, and generally updated the entire place. 

They also aren't as aesthetically pleasing as more modern systems and the radiators tend to take up a lot of floor space.

Efforts could include new, efficient, appliances and mechanicals, improved insulation and weatherization, benchmarking utility usage, renewable energy, backyard garden space, bike parking, proximity to public transit, good walk scores... you name it!

I use a local Allstate agent that insures my SFHs (owned by my LLC) with American Modern Insurance.

Now, its 4 months and you finally start thinking and taking all the advice that people who walked through gave you, like Jen the wife of Rodger and their two kids who said “I wish this bathroom floor was level, and a better tile was used, something more modern”.

Now, those benchmarks Brandon mentioned are for Washington, a much different market than metro Boston Massachusetts, my market.

That would be the benchmark in your case I would think. 

Thinking this would be a near worse case scenarioRehab PlanThinking I could possibly do interior upgrades, modernize the office into something appealing, (could be as simple as removing the paneling and exposing the brick, redividing the offices, updating the baths etc) and then rent out individual office spaces and charge $400-600 a mo for each office space - They'd be gross leases and I'd take care of all utilities, janitorial etc -- would not provide any onsight receptionist, fax machines etc -- each person would provide their own office equip -- I could potentially provide office furniture if needed, plenty of good used stuff to be found locallyThinking at a min 7-8 office suites, possibly more -- Per agent and my knowledge of community/research online I dont think a setup exists like this to attract possibly an IT person, a 1 man/woman business such as an accountant etc.  

In certain parts of Milwaukee, there are a lot of homes that could BECOME a more modern version of the old school polish flat style of living and would also double the units on a single lot.  

check Craigslist too for similar to benchmark values.