Most banks won't lend on an illegally converted property or one with inconsistent information vs the historic data.Back to original question- there are several steps for a conversion.

From memory (I may be missing one) I attended the retaining wall/historic site SFR flip (seemed like a potential homerun but I saw it took longer than projected but I do not know why), the add granny flat flip, the PB modified BRRR (Sarah's), and the new construction SFRs by the freeway.  

Maybe consider looking at an amortization table to see how much you'll have paid down the loans in year 2 and where that puts you versus what you think the house would be worth or what it's been worth historically (back between 2008-2009).

It's in the Historic District. 

This will ultimately depend on various factors such as: the bank you are dealing with, the loan amount, the value of the stock (or portfolio of stocks), loan to collateral value, historical price movement of the stock, probable liquidation value and quite frankly whether or not whoever you are dealing with has any particular intent to go through the headache of understanding what you are trying to do or get into what they'd have to in terms of analyzing or qualifying the asset as a collateral and any default related risk exposure.

If the lease is currently up at the time you prefer, and you've historically experienced very low vacancy when advertising the property at that time, it sounds like your downside is limited if you offer them a renewal and they decide to vacate instead, so I would lean to that.Another idea: A trick of Brandon and Heather Turner's, mentioned in "The Book on Managing Rental Properties," is to offer the tenant options.

Fewer, however, said their household income is significantly higher than it was a year ago.With the housing market now in its historically slow winter season, some agents are reporting activity is “frozen.”

@Pierce Wickens vacancy is almost zero if you are priced correctly and even some people are getting pretty high stretches for rent because we have a historically low inventory and super high demand.

Our current 52-week rolling rate is 96.1% based on the historic data.

In an inflationary environment, RE is historically good at keeping pace with inflation while other asset classes are not.