I briefly considered signing my STR over to an arbitrage group last year under much less favorable terms last year.If this suites you it may be advantageous.

I think there are two maybe 3 ways to look at this in my mind.  1) you go into it and bring it all up to modern standards but using that old charm to basically take what is there bring it up to modern standards and rent it out essentially I'm thinking cocktail bar or something trendy like that.2) most banks are on really good centrally located real estate if this is true, then I'd consider it for the dirt, plan to scrape the lot and go vertical with whatever the highest and best use is.3) a kind of combo of the two, if the lot is in a good location and its doable, pull the vaults or other "character pieces" out of the building, scrape the lot, and build whatever is best suited for the site there, but incorporate those historical pieces into the final designs.Is the site near a major retail area? 

The Condominium is high rise new building w/ high service luxury amenities including concierge services, valet parking etc.

He owns and co-hosts luxury STRs, and has a lot of great advice on what to look for and where to invest, how to be a great host or co-host, etc. 

1) Not blown money on cars, luxuries items, CC2) House hacked a 2-4 unit.

Commercial properties tend to yield higher returns but come with more complexity, higher risk, and longer vacancy periods, making them better suited for experienced investors.

Could be sooner permitting what comes on the market that would best suit us therefore this is where the HELOC would mainly help.

In this case the current financials on the property aren't great(rents well below market value and the owners family living in several of the suites) so the lenders will likely not provide the funding based on poor NOI.  

This whole thing reminds me of the commercial where someone tries to do surgery because they stayed at a LaQuinta Inn & Suite.     

In my experience strictly med buildings are generally developed in the same way as part of a campus or off the path a bit from the main retail corridor, so it really is only suited for that use.