Would love to hear some feedback from BP community managing medium term rentals and or get pointed to some medium term strategy resources.

It's on the water, and I have a 32 x 12 foot boat slip in the nearby community dock.

And like you note, if there is a lot of generic office space available in a market, it becomes a race to the bottom on rents, as well.While you can be close to bedroom communities, most offices also want convenience to amenities.  

It is in a 55+ community so my concern is that I would only be able to choose tenants from certain demographic.

Quote from @AJ Satcher: Hey BP Community!

So far, we have received this advise from appraisers in the Maple Heights area: 1) Attach all offers so the next appraiser can better understand the market value, 2) Provide a letter from the Maple Heights Building Department discussing the addition of the egress window making the bedroom conforming livable space, 3) provide comps for similar properties sold in the Maple Heights area (these do not have egress windows), and 4) create an itemized list of improvements and cost for renovations to the property.We are grateful to the Bigger Pockets community for their advice as well. 

Depends on community and amentities I'd assume. 

Welcome to the community.

BP is a great community with TONS and TONS of experience and knowledge to pick through.

Quote from @Max Wilhite: Hello @Dylan RobinsonWelcome to the BiggerPockets community!