or is the color what I am attracted too? 

I was attracted to your post because I would love to move to a warmer market that had a beach near by, in my mind that would do as much for me as buying a rental property.

3-4 families would definitely make more sense in terms of cash flow unless you rent room by room and there are very attractive properties in the secondary markets of Boston. 

@Ali Sardar About 50% of my business in 2018 was helping investors from California find more attractive investment properties here in Arizona.

Am I exploiting myself if I take the asking price, or it would be a better idea just to bid low first and see if the deal can be more attractive?

You want to attract the half that is not bothered by it.

One thing to watch out for is if this is a apartment converted to condo, sometimes developers have very low association fees to attract buyers.

Incentives only attract lower quality applicants. 

Whats the best method of attraction that’s going to make them say “I’m going to invest with him”.

Checking Yelp is a good way to tell if you have a good property manager some managers are really bad and seem nice in person to landlords but are awful at attracting/retaining paying tenants.