Originally a hotel - turned into apartment building by previous owner(s).  

I have read accounts of those in a similar situation who hired an attorney only to be tied up in court for a long period which isn't really an option for us as we are living in a hotel until our condo is put back together; and my concern with the public adjuster is that I would ultimately have to come out of pocket to pay their 10% fee.Second, I may have to sub out or even perform a portion of the work myself to stretch the money that we receive from insurance so that all repairs are accounted for.  

Also, we had a local cleaning guy who works for a three star hotel in our town come for three days to clean the bathrooms, windows, kitchen, refrigerator, walls and stuff.

There are a lot of unknowns that factor into that, like city regulations, taxes, competition from hotels, air bnb fees, and management/turnover. 

@Reggie Maggard There are a lot of hotel condo concepts out by the theme parks.

My question is - what are the major road blocks for making an apartment building into a 'remote check-in' hotel of sorts?   

We are looking at converting a 60 unit hotel into an assisted living facility.  

Instead of being held at a hotel, it is now held at a local restaurant.

Working on another niche I found that is, for lack of a better term, a couple red hotels.

On a serious note I do see many investors who have done flips on the residential side or own a few rentals and they want to now "dip their toe" in the water to start doing commercial.For many multifamily is something they understand from doing house rentals and that is where they want to start.If they feel more adventurous they will go for a different asset class (retail,warehouse,industrial,hotels,office,self storage,etc.)There is opportunity everywhere.The key is making good decisions on properties so that starting out you do not create a money pit that stifles further investment opportunities.If you buy right the property will help you onto others but if you buy wrong it will stifle you and sometimes put you under.