If you do not have a good CPA with extensive real estate investing experience I would find one and get their advice given your particular situation.

Welcome @Daniel Chi to the extensive world of REI.

I'd be hesitant to take this on given the numbers you're talking about, lack of relationships with local contractors and the extensive nature of what needs to be done and what you want to do to add value.

Bank won't release funds, bank doesn't release draws timely, extension need more equity, more reserves, etc.  5 years ago it might have been easier, but maybe not easy, just easier. 

It was an expensive and extensive remodel project but it worked out great because of the AMAZING purchase price!

As the Treasury continues to issue new bonds to fund Congress’ tremendous appetite for government spending, we should continue to see volatility in the bond market, and by extension, mortgage rates.

You may need an extension of time for your contingency removal.

Or is the 2 empty and now is a good time to do the roof extension?  

Courts are extremely friendly to tenants, give them numerous extensions, and bend over backwards to help them, so it's not uncommon to hear stories of tenants living for 6-12 months in an apartment without paying rent.  

Ask for extension on your other house.