But landed on flipping (with the intent of buying and holding eventually) given that I have always wanted to do it!

I have some land on the bottom of a mountain and the neighbors wells are only 200 ft deep, not on critical slope and it use to be farm ground with no rock to hammer for foundation/septic so when I eventually build there my costs will be greatly reduced and $130 to $180 a sq ft build cost could be realistic outside the cost of the land. 

Eventually, years down the road, I would like to sell some of the properties that I have acquired to pay off other properties and own them free and clear.

A tenant who pays late every month eventually doesn't pay then lives in your rental for a few months free.

This is my opinion only and Spark denies it but the details will come out eventually.

Or should I just hold onto it , hope if breaks even or has a small loss every year, and pray that it gets better or values go back up eventually.

If your goal is to eventually solicit from people who are not your friends and are looking for passive income, then you need to consider establishing a syndicate.

Additionally, I'm planning to commence my real estate investment journey by house hacking and eventually scale up to large multifamily assets. 

If you submit enough tickets and complain, long enough and loud enough, you will eventually get a phone call.

This is going to be my first STR learning experience if I eventually decide to kick start this journey, instead of just doing the buy and hold LTR which has less tax benefits.