Many banks handling tax escrow accounts for mortgages have mistakenly thought there was one tax due twice/year or totally missed one of the taxes.Investors should research the SEV and the Non-Homestead property tax millage rates to project what the property taxes will be after adjustment.

A Mortgage Broker oftentimes has an agreement with each lender as to how to handle submitted loans.

We draft the jobs ourselves, GC the jobs ourselves, avoid financing whenever possible, and I handle the listing as a licensed real estate agent, so we're collecting all the profit that can possibly be had on each job (aside from the fact that we try to not self-perform too much and mostly sub out the work).

i use Ownerrez to manage my rentals. it handles payments and i can do security deposits.

The key is to pick a lane—focus on improving as an investor, finding great deals, and letting a solid property manager handle the operations.

Would encouraging longer stays realistically help reduce this, especially for a medium-sized cabin?

Turnkey properties come fully renovated with tenants already in place, reducing the learning curve and allowing you to focus on growing your portfolio.You could also leverage local expertise by connecting with real estate agents and property managers who know the market inside and out.Feel free to connect if you want to discuss further. 

Read those relevant parts and figure out how far in advance you must give eviction notice, how to handle evictions with no lease, etc.2.

Quote from @Michael Challenger: I have no qualms with hard money lending, but I need to learn more about the process and structure to these for typical deals so that I am more comfortable and in a position to reduce my personal risk and risk to investors as much as possible.

Over time, we have developed systems to handle these situations as effectively as possible.