The repair costs will take multiple years to recoup and with the age of the property I'm concerned if it's even worth holding long term or get out while I can before I fall into a money pit and get stuck.  

I think this is a modest goal, in this day and age. 

Moreover, even if you decide to go the commercial route, given your age and current position, I still highly recommend the investment strategy of house hacking.

Great job starting at such a young age.

In this day and age, not having a online Prescence and clearly documented track record is just a huge red flag

I wonder how it may work this day and age.

One thing that got me was the age of the water heaters.

I would have to radically change what I am doing to have a significant effect on that age (e.g. go from investing 1k a month to 5k/month). 

My post didn't age too well.

@Javier Parra Garcia..not to hijack the thread, given the age of it, but wanted to respond here.