@Toure Smith

It depends on how well the building has been maintained. Try to get as much information from the seller/listing agent as you can regarding the plumbing, HVAC, electrical, roof, exterior maintenance, etc. Getting a home inspection should also help you see if there are problems with the major building systems.

Homes built before the 1950s, especially those with balloon framing, knob-and-tube wiring, or galvanized plumbing, often require full guts. If the home has been updated in phases over the years, you might be able to get away with a partial update.

You'll want to lean on a great contractor for more expertise though. Maybe connect with @Jonathan Klemm?

I generally agree with the advice to start with smaller projects. Start cosmetic and then take on bigger rehabs.