Advise sought for first time investor

[Kevin Paglia]

I am hoping to get my first investment property inside of a couple months.  I am torn between two options for me.  This is for a house hacking quad-plex.  

First would be minimum work to get ready kind of place.  Update the floor/kitchen/bath kind of place.  higher purchase price, lower forced equity getting out of it, but it gets my feet wet and learn in increments.

Second would be a house no one else wants to touch kind of home.  A LOT of work to get livable, and months before renters could move in.  Days and nights spent fixing it, working with contractors daily, and possible lending issues due to it's physical state.  But in the end, lower initial cost, a lot of forced equity out for the next purchase. Scary part is thrown into the deep end to learn.  No incremental learning, just there and have to swim.

I, honestly, lean for the option 2 simply for the equity out in a year when the house hack expires and I can move on to the next one.  a refinance on it would make buying 1-2 more units very possible.

So... hit me.  Opinions?  remember back to your first investment and best advise for a noob...

[Kevin Paglia]

Thanks @Joseph Cacciapaglia, Your last line hits on something I told kids when i coached sports,  "Success brings confidence, confidence brings success".

It has taken just a few months to save for the first house hack.  Technically, i could buy a property in May, depending on a bonus that may be in limbo due to the virus.  If not then by July I will definitely be able to buy one.  House hack with a couple hundred profit sounds real good right now, knowing in a year when I move out that profit jumps.  Option one does allow that most of the cosmetic updates I can do myself which is good.