I have worked with the City of Tampa planning and building dept to get plans approved and permits expedited and ran the construction site myself.Happy to connect if you have any questions about Tampa.

All of our leases have this clause in it "Overnight guests are permitted.

I also haven’t had to deal with the court system but when dealing with the City of Stockton for permits, they’ve been great and fast compared to some surrounding cities!

Here's a list of stuff that went wrong because lack of experience costs time/money when you do a DIY project:Car broke down because I used it as a truckHad to get a GC registration with the state of Rhode Island or face violations from the building inspector (5 hour course, pay for insurance, and taxes, around $2000) because here you can't pull permits yourself for anything and you need permits for everything other than painting or putting up shelves. 

I did all of the work myself, fully legal and permitted. 

The permit and environmental process can potentially be a nightmare. 

A STR that is in a good and allowed area can make 3 or 4 times what a LTR makes in a month.A calculator can't tell you about an area, amenities or local attractions.It also can't tell you if it is legally permitted to be a STR.

Owner financing was also the better route for both parties as a result of dealing with the state in transferring permits and operating rights on the water well and sewer system, which is a slow and arduous process.

@Mallikarjun Reddy Pateel  I would also ask for city permits signed off by every department (HVAC, electric, plumbing etc). 

Asheville has a near-ban on all Short Term Rentals, so don't even look in the city limits because it's almost impossible to get a permit.