So eventually this negative cash flow property becomes cash flow positive and pays for itself including property taxes, hoa, mortgage etc.Trying to calculate how bad is my investment here or should i sell out if there is appreciation 

And start from a position of strength rather than getting into a property right before you go back to finish up school and have no income for a year.

I figured this could possibly put me in a good position for a cash-out refinance when I’m ready to move on to a second property.If I stick within my budget, Philadelphia seems to offer the most housing availability, but I’m concerned about most houses available being in rougher neighborhoods.

As we continued to scale, we eventually added a positions to start taking some of my wife's responsibilities. 

I agree that demand and the house staying dry during Hurricane Milton were positive signs.

I’m in a similar position with similar goals.

So far, it’s 100% positive.  

You’re in a solid position with this property, and it’s smart to weigh your options carefully.

However, when you don't know what you don't know, this is an incredibly dangerous and risky position to be in with such an expensive investment.Just my 2 cents.

I’ve been in a similar position where I wanted to scale but equity was a limiting factor.