Information Overload - STRs vs Fix n Flip

[Michael Sassone]

Hey everyone,

I've been educating myself the past few years on REI and feel like I am experiencing information overload and would love some advice/guidance from some experienced investors.

I'm trying to figure out which type of investment appeals most to me and my goals - it seems they all do and have different pros and cons that come with them when I sit down to analyze.

Like many, my end goal is to escape my 9-5 and be able to live off of my real estate investments. I am currently a Merchant Mariner and was previously spending 8-10 months a year at sea. I was able to get a job on a gov ship through my union in Baltimore that allows me to be home and have weekends off which allowed me to have time to move closer to my goals. 

In January, I purchased my first out of state investment property in Tennessee. The house is worth about $230,000. I paid $90,000 cash so there is no mortgage (my mother in law passed away, she had no mortgage and I bought my brother in law out). 

So as I understand it I have access to 80% of that equity $184,000. 

This is where I am having trouble figuring out which direction I should go - I am a REALTOR and a Licensed General Contractor so I have access to MLS (am also working with 2 REALTOR's who deal specifically with investments - one deals with STR's in the Nashville, TN area the other deals more with Fix and Flips in the Baltimore County area). As a General Contractor I can do all my own work and get significantly discounted materials.

STR's appeal to me because of the quick ROI especially in an area like Nashville.

Fix And Flips also appeal for similar reasons but seem to be a lot more involved. 

What I am unsure of is the different ways I can finance a deal and which would be the best way for my goals and situation. 

Would I be better suited trying to find a Fix N Flip, pay cash using my equity, do the work myself and then put it back up on the market or would I be better off purchasing an STR with 20% down and leveraging a loan to get some cash flow coming in then maybe pursue a Fix n Flip using the remaining equity and let the STR repay the HELOC until I sell the flip?

My credit score is above 700, I don't have much debt (5k on a credit card and 20k student loans). 

There's a lot I'm not adding to this post for the sake of keeping it short. Would love some guidance or to hop on a video call and pick someones brain.