Those areas usually attract crappy tenants who don't pay rent. 

Competitors, local events that attract crowd, pricelabs, seasonality, weather events, your unit profile..

If I went to the investor and said "hey, I'll pay you $x amount per month to keep living here with the intention of buying it later" would that be an attractive offer?

I can't speak of other type locations, but here by the beach, a tiny home located close to the beach can be a very attractive rental.

Tends to attract a younger /trendy crowd.

These markets will rise until either a bunch of new supply starts coming on the market or there is a shift in population trends.Focusing just on cashflow often attracts people to areas where there are other problems.

Instead, focus on attracting the right folks who align with your investment goals.

When you do the math debt-free is not all that attractive.

There are many high demand section 8 communities in Michigan because not all landlords cater to section 8 so tenants are happy and stay if you provide attractive housing for them.To Your Success!

Potential Middle Ground: Consider Renovating: Instead of selling, you could do a light renovation on the older property to increase its value and attract higher rent.