Thanks All for you comments.

Your comment has been insightful. 

Please put your input on whether or not this seems feasible, I need the good comments and the criticism so I know exactly what to expect in the worst case scenario. 

@Dax Squillante  You really did not provide alot of detail for others to comment on.

@Aaron Ingram$5000-10,000 for a design, construction documents, structural work, permitting and dealing with any city comments is pretty typical for any size project.

Update for everyone,I wanted to respond to each comment, but I can't figure out how to @ each person in 1 reply and don't want to spam 10 replies/My lease states something along the lines of "On this day July 16 2021, Derek S. and ABC tenant enter in an agreement for..."

The main property is a 2 family that’s occupied and creates good cash flow, my only reason for selling is to realize the equity and use it for a renovation elsewhere.I look forward to hearing any comments or suggestions.

Pay all previous and current property taxes, pay the planning fees, record the new plats, wait for the new property tax numbers to be assigned, go through the neighborhood comment meetings and all other processes involved with zoning.The other hurdle was getting the lender to sign off on the subdivision.

Most comments here across the country are the market is hot so just curious if your market is really slow or if there is an issue with this home? 

actually that comment on qualifying for a vacation rental on your income and not relying on property income that I made to @Kenneth Garrett  I meant for you.