STR's are risky, local regulations change, the economy goes bust, or the area your buying in become less desirable over time and your running into issues.

I did not mean that Section 8 should be treated differently, I added that info in case there was some regulation that I am not aware of that may change people's thought process. 

Costs us about $160 a year and includes filter changes.

On the flip side, entering the short-term rental market demands caution due to tough competition and changing rules.Flipping the basement could be a game-changer, but you'll need to handle construction costs, time commitments, and market uncertainties.

My property is already in an NY LLC, can I just file a Certificate of Amendment or Change with NY and be on my merry way? 

LLCs do not change anything for taxes.Also, there're no tax benefits for renting out a room.

I'm interpreting "alteration" to mean any change to the existing unit but perhaps that's viewed differently by the jurisdiction that "alteration" means any change (such as new construction) on the lot?

If something does need corrected, they will give you a couple weeks to make the changes and do a re-inspection, or you can tell them at that point you don't want to move forward with the program at that property and end everything there. 

You would most likely need to just refinance with the VA loan and have a transfer deed changing ownership at closing. 

Use the enemy method to check your prices change  your photos up.