First, if you're generating a positive net income, the Schedule C is the safe choice because you're paying more tax (specifically the self-employment tax), so you can't be faulted for tax avoidance as you could be if you improperly use Schedule E. 

Is it a mater of morality or legality? 

What legal parameters would you be cautious of?

Does anyone in Florida or specifically Daytona Beach have any experience working with code and obtaining a rental license?

As far as your specific question goes, I don't think the banks will count the rental income on the house in FL towards your income requirements for the new mortgage because you are still living in it, but that's a question you'll need to ask your lender to be sure on.

Not sure about Seattle specifically (it may be more generous), but changing SF zoning to MF and having a new meter put in, etc. can be a time consuming and lengthy process.

Specifically, it sounds like all interest payments made are fully deductible because, in this case, the individual unit's balance cap does not apply (because it is grandfathered) and the underlying co-op mortgage's principal balance allocated to the specific unit is below $750,000. 

No legal headaches.

The kitchen is what's sold me in my first house and it'd a great lay out in my current house.My next house I'll be a bit more specific - bigger deeper sinks, pasta faucet even if I only use it once a yesr for a big jug of summer iced tea lol and a dishwasher, walk in pantry are on my check list.I feel other amenities like skylights or big windows, cellars for dry storage would be cool too but I'm not really a big baker or canner lol.Now it's got me thinking - imagine a hidden island?

Our agreement is for a structure shared by two properties, but we have found signification  cross-over from Private road maintenance ags.think this is too specific - google only came up with a couple free samples we could review.Any outlines from experience also helpful.