Even at $2500/month I pay currently for rent would it be worth it to take on this venture or should I look out of state where I could conceivably buy several properties for the same price even though I’ll lose the FHA and have to do the full 20%?

What is the income you are losing by delaying?

Tenant will need to pay only the amount of rent the landlord loses because Tenant moved out early.

I'd emphasize that it's not safe for her to live there in the current condition, the city is going to start charging for violations and you can't allow it to continue.In your shoes, I would loop in the Housing Authority caseworker because if she gets kicked out and/or doesn't pay her rent, she can lose her voucher, which would further add to her issues.I have generally found that empathy goes a long long way.

If you jack the rent too much they could say F it and stop paying and you would lose out on a years worth on rent because they refuse to leave and the eviction process in CT is a pain in the ***. 

In that case go right on ahead since you're not losing money. 

If you wait you losing your most precious resource… time… compounding money… in 1-3 years you should have your 25% for your next investment property.Don’t overpay and make sure the numbers work

I tend to think any GC that would do that is shorting themselves and losing control over the project.  

Repairs usually come at the most invconvenient times and expecting them to expedite a repair so you are in compliance with habitability covenents is a losing battle.

My concern, I feel like if I don't make a shift somehow, I will lose potential deals in the future as a result of not getting the needed approvals.