I would really appreciate any advice or critique as my main concern was the chronological structuring and also if anyone knew the time table of refinancing a FHA loan even after repairs) If anyone experienced has any insight to refining this plan, I greatly appreciate it!

Since it sounds like your property is owner occupied first (it's still your residence when you travel for work), have you gotten quotes as your residence and then added the rental use for the ADUs and part time your main home? 

- Initial capital infusion was too low and ideally I would have budgeted for more startup expenses; this is mainly due to the four renovations and HVAC issues.- Would have inspected all HVAC units and used failing HVAC systems as negotiation point (two HVAC units failed within one month after purchase).

I’m mainly looking at Point Breeze/Grays Ferry and Brewerytown areas.

We installed them in the main home and the ADU for a fraction of the cost I was originally quoted for the ADU alone.

I received bids between $4,200-$5,700 for water service update (Replace 5/8" lead w/ 1" copper & tap into main line).

I have bumbled through properties sales, rentals, mortgages, etc. mainly because of moving so much with ex. 

I personally fall under the monthly income increase that come from rentals so that's my main concern.

You need to figure out a plan on how you plan to attack one or more of those target areas.

Depending on if the attic is in the main structure or the ADU it will be valued differently.