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.

HOA Fees (if applicable)7.

Renting the house out may be because some HOAs do not allow STR or cap a percentage of it to be leased.  

At the very least you could sell those townhomes 1031 and purchase 8 single family homes and increase NOI by maybe $1000 - $2000/month just by getting rid of HOA.