It is more expensive but may not require an appraisal and can close in a couple of weeks. if I can wait then I use the most competitive rehab. lender after obtaining multiple quotes. 

I'm not a fan of flipping simply because I hate paying taxes when I don't have to.

Lots of people who have trailers don't own the property they are on and sell them.As for the owner of the land expecting tenants to do repairs-there shouldn't be many repairs required to the land, just the trailer that is on it (which your grandmother owns and should be responsible for maintaining). 

It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

Does it require a highway occupancy permit if its on a state road, in my area it cost me around $1000 just to get the permitting and design for my driveway entrance.

Negotiations focused on securing the property at a favorable price, enabling us to achieve a profitable margin in a highly competitive market without requiring additional renovations.

EDIT: Can't delete this post, so simply editing it.

You're going to have to scrap like crazy to break even - think rent by the room, short term, mid term strategies that require more work.

If you are using a loan, well there is simply no inventory in Cleveland.

As Jonathan mentioned it can be done, but they may require an appraisal of the property.