Real estate attracts a different culture of people / professionals all together.

The art of wholesaling is to get the properties under contract at a price that is attractive to investors.

I do have some experience in remodeling so fixing and flipping is also attractive to me.

And, I wasn't suggesting that "being honest" required you to agree with me.Good luck finding a Lender who (also) doesn't agree with me (with attractive Interest Rate / terms)!...

If we decide to move forward with offer/purchase, I would like to make a few updates to the vacant 4-bedroom unit (pics below) to maximize rent and attract highest quality tenant possible. 

Wow, this is a good discussion, @Christine N.If you were able to line up and attract clients from other sources besides Airbnb, VRBO, and TripAdvisor then I think you would have a very strong business proposition. 

You sound like you know some things about RI investing ;) I think we've narrowed our search to the Middletown, Newport, Portsmouth, Tiverton, Bristol areas, nothing west of the islands because of the toll bridge and tourist traffic.

Other factors such as bedroom size and layout or even the condition of the neighborhood all play a huge factor in the rental value and attractiveness of the home as those are the factors that tenants look and pay for.

Even a 4 bed is likely to attract families with more children. 3 bed are the most ideal as rentals. 

Attracting institutional buyers looking to deploy capital in a stabilized asset in a thriving market; Florida at the market going cap rate.