If it is to compensate for credit issues - the maximum deposit(including last month if permitted) and month-to-month lease may be the best idea from your side.  

A skylight would not count as an egress "window" cannot be more than 44" off the floor.You can be pretty much certain that social housing (Section 8) will not permit the room to be counted/used as a bedroom.If you have not yet made an offer on the property, run your analysis as if it had one less bedroom and generated the according amount of revenue.

Got permits and licensed contractors for the job.

If they added equipment (AC, computer, whatever) that the systems were not designed to handle, that could be a fire hazard (violation of code) Do they have pets, and are not permitted?

Nor is it easy to install countertops or wall cabinets by yourself.You'll need a plumber to move the gas line.And permits.

I value a real property attorney's perspective, just don't want to set aside thousands for retainer just for exploration on whether I have standing.If that is not an option, it seems to me the next option would be to incur all of the costs, try to consolidate the parcels with the highway taxing districts and then seek out a permit from the city to build an Accessory Dwelling Unit under their standards.

Also, unless you're getting a killer deal on this unit, it might be worth considering some units that are already STRs, to save the cost of furnishing, preparing for STR, permitting - if required there, and the long process of building of repeat guests and occupancy...

I been trying to obtain a permit for a septic system placement by the Duval County health department with the help of my septic contractor for 5 months now without no success.I already spent hundreds of dollars for numerous property surveys, lend measuring, permit requests and more.

Some fix up is ok but I require properties to have been properly zoned and permitted, and that most major fix-up areas not an issue aka: solid electrical, plumbing and foundations.

If the asset is incorrectly classified, this mistake could cause an overpayment in taxes.Compliance Issues: If you fail to meet certain compliance requirements such as permitting, licensing or regulatory requirements, this could trigger large tax penalties.