You don't mention the listed price of the unit ... but this amount would seem high ... every property/ complex  is unique and HOAs can be difficult to match up ... the other issues to consider too are 1) possible future assessments that aren't able to be foreseen 2) future possible litigation that might occur 3) resale appeal in the future 

So, to a buyer, the new homes may be more appealing, reducing the appeal to my house.Therefore, option A is:A.) 

@David Stumpf the MDF siding installed does not have a painted finish ideal for this environment and the color is just ugly with no curb appeal.

I would suggest you make it appealing to the seller but also ask them from the start if that's something they would even consider. 

BUT companies will advertise a property as being maybe an A- when any local would tell you that area is a C.A good first step is just looking at the property and the neighborhood on Google Earth and seeing how the property looks, is the house unkempt, how appealing is the neighborhood, etc.

No property taxes are generally assessed on their own on the normal schedule, and you can appeal them anyway.

Getting into a small multi family where I would reside on site appeals to me a lot even though I don't necessarily need to live on site but would work.I have about 30-40k of my saved money to get started.

It’s a much richer look that definitely improves curb appeal and value.

DBA is really just a title, it doesn't offer the same legal protections that an LLC or S Corp does so it is really only necessary if you are trying to appeal to customers.

I know I'll be doing some renovation work to make it more appealing since I want to turn it into a short term rental that I'll actually own.