So we're fairly new to real estate investing and will potentially be working with an out of state wholesale brokerage in Tampa FL for the first time.

If I'm going to sell a chiropractic practice (30+ year successful business) and carry the financing for the buyer, what would be a fair interest rate over a 5 year term?

It's Definitely not fair to ask them to do that simply because you are unable to move in on time, even if that is not directly your own fault either.Definitely try to negotiate with the landlord to try and recuperate some of that deposit and maybe see if they might know of any openings for you come January.

Of course, at the end of the lease, it's fair game and I often find it best to change out the tenant as we might be in a value add, raising rent and just wanting to start over.

But it seems like securing financing for this kind of deal would be fairly straightforward as long as my financial situation supports it.

Fairly new investor here, working on first purchase of a property to use as STR, and hoping I didn’t get the cart before the horse.

This mainly pertains to your roof - IF you have an RCV policy - do not switch anywhere else -- that is a good price and a good policy -- if it's ACV you can shop around -- try Shelter too -- I worked for them - all my coworkers were fair -- I just wont get a policy there -- something to do with not ******** where you used to eat and if I had a claim it'd be weird to deal with my former co-workers -- would rather deal with people I dont know. 

Mine is fairly “local” for a 30 mile radius despite there being about 8 different towns.

I would also like to know the fair market value for rent per square foot in the area.

Steady income, but the property is earning well below fair market rental rates for the conventional rental tenant market - roughly ~$500.