The house was built in 1990 but it not modernized to say the least; the interior still looks like you are in the 1990s when you walk inside. 

Due to multiple issues stated above, my insurance lady (previous 20+ years in underwriting) has told me to buckle up for a few years of this before we see much changing.

Yep, clear as mud...And, I actually met the person who wrote the modern-day ("simplied") tax code.

Or your cleaning lady:

In modern houses nothing.

We did replace the coffee table and two end tables with something more modern and light.

Would you send a cleaning lady or simply send your handyman to replace the door and expect tenant to clean up the glass? 

@Ben Kappel said it best, it's similar to modern dating.

Your main possible issues will be 1) Electrical - probable old wiring, some will have been replaced, but probably multiple splices and a lot of jury-rigged circuits. 2) Plumbing - probably old sewer lines, most interior locations will have been renovated, but check everything.The other things we look for may have been recently replaced or repaired.....because they have to, like roof and HVAC.Structure may be an issue, have it checked, but after 100 years it might be ok, it will certainly not be not up to modern standards, but who cares....Just get a thorough inspection, for something like this I would get an inspector who is also a GC...

Hey guys I have a killer deal on a pocket listing from an older lady who wants to move into a retirement home.