It isn't like this a condominium where assessments are paying for common parts of the building like the roof, etc.Prior to this, I didn't have much experience serving on an HOA board and have therefore relied on the management company for their opinion on certain decisions. 

In my opinion, the hardest part of STR is getting it up & running.

That is cheap to install 2 units in my opinion. 

In my opinion, the answer to your question is "Unlikely". 

I have noticed quite a few posters lately that are requesting help, opinions, prices and information on their properties where a good answer would require either the square footage, the location or both....and they provide neither.

In my opinion, the easiest path to investing in real estate is house hacking a 2-4 unit multi-family property.You have the right idea of getting around other like-minded investors. 

In my opinion, even if you partner with a local PM company or turnkey operator your returns will drop significantly.

Charleston (in my biased opinion) is one the best places to live in the country.

Definitely can be a lot of moving parts, but it's crucial (in my opinion) to learn and be honest with yourself about even liking rental properties. 

Just know that I respect the opinions of everyone.