But given that the renovation was done such a long time ago, there are some wear and tear, like Window and HVAC, shower handle and stuff, so we have been updating those one thing at a time, and I'm hoping that this house can handle another 20 year so the $ we poured in for the new set of windows are worth it...Would appreciate any thoughts!

Some stuff you can get an "estimate" for from a GC just off the square footage. 

Also, I think a newer building would make my life as a landlord a lot easier since I don't have much experience and wouldn't have to worry as much about stuff breaking down all the time. 

Stuff like that cant be unseen - if something unfavorable is discovered, it's permanent. 

In general, I don't think just running stuff through there will get it done because you won't be earning enough to make it loan-worth anytime soon.

Its why i travel to the Market I spend usually 2 to 3 days my office does a deep dive into MLS stuff..

Deposit for another place + $ to actually pack up and move his stuff.

But, romex that hasn’t been properly secured to a beam, is kid’s stuff. 

For general real estate stuff (including evictions) I have worked with Harry Kalogerakos, and Raymond DeBates, both are good, reputable attorneys. 

BTW, I am not a real estate agent so can't help you with agent-related stuff.