Do you know of any other complexes in Durango close to town where HOA/city restrictions would allow us to rent out nightly more than once every 30 days? 

We had actually gone under contract but then backed out due to the strict guidelines of this buildings HOA when we went in for an interview. 

Unfortunately, even though I have a tenant that is covering my mortgage, I am losing several hundred a month due to HOA fees.

Just make sure the HOA has enough funds. 

HOA - 89.00 a month

I know doing this in an HOA is probably not going to happen, but what other situations should I be aware of?

However, every time I get an inspection HOA is charging me for it.

@Matt LuteyI agree with @David Robinson but before you go there, check your condo regulations (HOA).  

Everyone I talk with has agreed with me what a shame it is to want to get rid of such a great property for the unknown of condos and their HOA fees especially considering prices in CT have surprisingly gone up significantly since Covid with so many NY’ers fleeing the city.

I would also add read HOA Covenants, Conditions & Restrictions if the property falls in an HOA.