My suggestions would be in this order:(a) Determine the type of financing you qualify for - this will short cut the process considerably and save time on investment angles and next steps.

If your market is leaning more towards shorter stays...which does seem to be the current demand nationwide...I would not cut your properties out of that demand!

Those things won't matter if your business crushes it. i feel like it would matter when those things add up and start tearing at ur profit If banking fees cut into your profit, your profit isn't big enough.

But most of these bridge loans have future funding components where the lender will fund renovation work as the work is completed and add that to the loan balance. 

First step is always to cut the water source and fix the leak asap.

I think the folks that pay for these programs have the wherewithal to simply cut a check and its no big expense to them compared to what they stand to get out of it. 

If not, cut it all out and put down some strong sturdy plywood.

It would be nice if you had a contact who was an actual mason not a marketer.  1930's construction is rare so maybe they cut some corners it was a global depression.  

Cut rates until it rents.

Focus on the big moves: security, renovations, and cutting dead weight.