If you don’t need the cash and are an Accredited investor, you could 1031 the boot into a Delaware Statutory Trust and defer all tax.

Quote from @Craig De Borba: Welcome!

I am focused primarily in MD and DE.  

@Robert McCormickI quickly looked up some info for Sussex County yesterday and was going to post it here, but then realized that was for Sussex County, DE, so, obviously not applicable.Anyway, it seems like you already found some info on the appeals process.

I think like @Paul De Luca pointed out...it's hard for us to speak to your specific deals if we don't know all of your numbers, your criteria, and your exact situation.My opinion would be to go for it! 

I would recommend @Paul De Luca as an experienced agent with house hacks in the Chicagoland area.

Also, keep in mind De Minimus Safe Harbor is available on remodeling expenses with an individual transaction value of $2.5k or lessAlternatively, for any of the remodeling costs in Step 1 that don’t qualify for De Minimus Safe Harbor and have a useful life (period they will take to wear out) of 20 years or less you can take 80% bonus depreciation in 2023. ...

@Zachary McHugh the best research you could do in New England is attending a few local selectman committee meetings to hear, first hand, how such small committees operate and how quickly they can enact de facto STR bans within their community.

I am going to rent a room out in one of my units too so I should have no problem living for free (hopefully taking into consideration all expenses)Originally posted by @Paul De Luca:@Brandon GatesThe first house hack is mostly about lowering your housing expense and gaining momentum for your next deal.

I think you overpaid for the property but at least you took action and didn't spend years reading books and watching videos.I think de-listing it then list at again in March as a fresh listing or lower the price.