Here's the bottom line:The biggest concern is the downtime (~4 mos.) and costs just to pull all the permits, etc.

I bought a house hack str via a 203k in Bradenton, FL and have been renovating extensively over the past year while living in it.. i didn’t realize I was supposed to cost segregate before I started renovating or renting it out- permitting has been a nightmare so it won’t be finished for another month and I have been holding off on tax filing for exactly the reason Bonnie spoke about..

.- always have strong reserves for repair, factor in everything from tree to fences- make sure your HVAC is caged- when you purchase OOS, make sure you understand the city regulation, is there a permit issue or something like that.

But unless the lot has direct access to roads and utilities will still be considered unbuildable, and the government may not issue permits until infrastructure is complete2: Roads and utilities are installed.

Estimated cost to design, permit, and build?

Curious if you pulled the required permits?

Do the math plus add other unknowns such as permits, changes in the deed, along other expenses.  

My last rental I purchased in Nashville had some pretty strict regulations on which parts of the city qualified for a short term rental permit and which were blocked off.Does anyone know of regulations on permits/city codes there?

GC charged $2k as a retainer, went ahead and put water/power in their name, Filed for permits, ordered dumpster and portal potty, and hired demo crew.  

If you wish to rent your home for stays of 30 days or less but for more than 180 days per calendar year, or the property is not your primary residence, you must obtain a use registration permit for a “Visitor Accommodations” use.https://business.phila.gov/limited-lodging-regulations/