Tools like Rentometer, Zillow, Cozy Rent Estimate, etc. are good - but rely on there being similar properties in the area.The best solution is to get a really good understanding of what your competition is renting their places for. 

Solution: maintain the formalities and keep the limited liability.- insurance company lawers will only represent individual not llc:  Insurance defense lawyers will protect the insured, regardless of the form that policy holder takes.- forced to use commercial loan, which has higher rates:  Depends on your situation. 

What other solutions are there?

So keeping it properly caulked will help, but the likely the only real solution would be to rebuild the shower pan and up the wall. 

When vetting your PMs, ask the questions that might provide solutions to these problems.Solution to #1 – you are looking for full transparency.

Is this the right way to think about this situation or is there another solution?

Hello @Justin Furtado an ADU is a great solution because of California's new laws.

The furnace was in fair condition and did not require replacement so I came up with an innovative solution.

You should also make sure that the Qualified Intermediary is not going to try to sell you replacement property solutions in order to earn additional revenue. 

Another potential solution is getting an oil burner that is more efficient and auto fills.