Here are a few things to keep in mind:Eviction Process: Courts often prioritize tenant rights, and during certain times of year (like the winter months), it’s tougher to get an eviction through.Legal Barriers: If the property is rent-stabilized or the tenants have protections, it could mean additional layers of complexity. 

Winter doesn't bring too much extra cost as long as the home doesn't have outdated appliances and has sufficient insulation.

I'm taxed in the highest bracket but even if you are not, every extra dollar you bring in puts you closer to the next tax bracket.

I turned the extra room without a bathroom into a workout room as a bonus amenity.

3-year PPPs are usually reasonably priced while also shaving off those extra 2 years...if you drop below 3, rate/cost can get a little gross.

The only real offer I got through FF was for $1700 a month, and I'd rather leave it empty than take that and pay for the heating bills and the extra wear and tear of long term renters.

Do an assessment of value now and after you get the ADU permitted * We have been in situations where $8k for permits could mean an extra $100k in value or $2k per month in rents. 

I'm considering converting the shed into a DADU to maximize the use of the space and earn some extra income. 

According to the pictures it looks like extra trashy place.

There was also extra bracing to keep the roof from moving further apart.