I'm just getting started in my Real Estate Investing Journey and looking for input from other investors with experience in NJ or other similar crowded/ expensive markets. I'm living in a single family that I'm renting, the house has sentimental value to my landlord since it is her childhood home. The house has not had much upkeep/updating done, and needs some repairs. It's also still full of my landlord and her families stuff (old Furniture, clothing, junk, tools, pictures, etc). My wife and I have been living in the house for 5 yrs and she has been very very very slowly moving out some of the furniture and junk allowing us access to more rooms, while talking about possibly selling the house. The house is large for the area (3 story w/ finished basement and detached garage. 6 bed 3 full bath) and requires lots of upkeep in its current state, and is in a flood zone as it is right on the river, but it hasn't flooded.

I'm trying to figure out how to start analyzing the property to see if it would be worth purchasing and fixing up while living in it and then turning into a SFR or buy and reno/converting it into a MFR. The house is in Paterson, which has high taxes, crime and a troubled school district, but it might be a candidate for Section 8 Rental. I can do most of the repairs my self with help from friends and family. I don't have any experience with Section 8 Rentals, but read some articles about how if done correctly it can help to create some stability since the rent is paid by the federal government. Any input or discussion would be greatly appreciated.